Category: 3438-16-2

Synthesis of 2-methoxy-5-chlorobenzoic acid and its ethyl ester was written by Przytycka, Roza;Malinowski, Stanislaw;Wirecka, Elzbieta. And the article was included in Roczniki Chemii in 1954.Reference of 3438-16-2 This article mentions the following:

Reduction of 2,4-O₂N(Cl)C₆H₃OMe with Fe and HCl gave 71% 2,4-H₂N(Cl)C₆H₃OMe, which treated with NaNO₂ and HCl, and then with Cu₂(CN)₂ gave 82% 2,5-MeO(Cl)C₆H₃CN (I), m. 99-100掳 (from alc.). Heating I in a water-alc. solution of NaOH gave 51% 2,5-MeO(Cl)C₆H₃CO₂H, m. 77-9掳 (from alc.), which heated in an excess of EtOH in the presence of H₂SO₄ gave 58.8% 2,5-MeO(Cl)C₆H₃CO₂Et, m. 98-100掳 (from EtOAc). In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2Reference of 3438-16-2).

5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) belongs to organic chlorides. Chlorination modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than water due to the higher atomic weight of chlorine versus hydrogen. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.Reference of 3438-16-2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Structure and absolute configuration of some 5-chloro-2-methoxy-N-phenylbenzamide derivatives was written by Galal, Alaaeldin M. F.;Shalaby, Elsayed M.;Abouelsayed, Ahmed;Ibrahim, Medhat A.;Al-Ashkar, Emad;Hanna, Atef G.. And the article was included in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy in 2018.Safety of 5-Chloro-2-methoxybenzoic acid This article mentions the following:

The absolute configuration of 5-chloro-2-methoxy-N-phenylbenzamide single crystal [compound (1)] and the effect of introducing -[CH₂]_n-, n = 1,2 group adjacent to the amide group [compounds (2) and (3)], were studied. Furthermore, the replacement of the methoxy group with a hydroxy group [compound (4)] was defined. Proton and carbon-13 NMR spectrometer were used to record the structural information of the prepared compounds X-ray single crystal diffractometer were used to elucidate the 3D structural configurations. Intensity data for the studied compounds were collected at room temperature The X-ray data prove that compound (1) is almost planar, with maximum r.m.s. deviations of 0.210(3) Å corresponds to C13. This planarity starts to disturb by adding -[CH₂]_n-, n = 1,2 groups between the NH group and the Ph ring in compounds (2) and (3), resp. By replacing the OCH₃ group by an OH group in compound (4), the plane of the chlorophenyl moiety is nearly perpendicular to that of the Ph ring. Such new structural configurations were further illustrated by the IR, and UV-visible spectroscopy measurements in the frequency range 400-4000 cm ^-1 and 190-1100 nm, resp. Spectroscopic analyses were verified with the help of mol. modeling using d. functional theory. The estimated total dipole moment for the prepared compounds reflects its ability to interact with its surrounding mols. The higher dipole moment for a given structures is combined with the higher reactivity for potential use in medicinal applications. In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2Safety of 5-Chloro-2-methoxybenzoic acid).

5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Safety of 5-Chloro-2-methoxybenzoic acid

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Sulfonyliminoimidazolidines. A new class of oral hypoglycemic agents. 1. 1-[[p-[2-(Acylamino)ethyl]phenyl]sulfonyl]-2-iminoimidazolidines was written by Schweizer, Ernst H.;Maerki, Fritz;Lehmann, Claude;Dietrich, Henri. And the article was included in Journal of Medicinal Chemistry in 1983.SDS of cas: 3438-16-2 This article mentions the following:

A series of 1-[[p-[2-(acylamino)ethyl]phenyl]sulfonyl]-2-iminoimidazolidines were prepared from I (R = H). Compounds from this new class of oral hypoglycemic agents lowered blood glucose in normal and in streptozotocin-diabetic rats. Potent analogs were obtained by modification of the acyl residue. I (R = trans-MeCH:CHCO) was the most potent compound in the normal rat (20 times tolbutamide), and I (R = 5-methyl)-3-isoxazolylcarbonyl) displayed the highest potency in the diabetic rat (similar to phenformin). Structure-activity relationships were discussed. In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2SDS of cas: 3438-16-2).

5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) belongs to organic chlorides. Chlorinated organic compounds are found in nearly every class of biomolecules and natural products including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids. Organochlorine compounds are lipophylic, meaning they are more soluble in fat than in water. This gives them a high tenancy to accumulate in the food chain (biomagnification).SDS of cas: 3438-16-2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Identification, isolation, synthesis and characterization of isopropyl ester impurity of glibenclamide was written by Pandey, Lawanya Lata;Sarkar, Swagata. And the article was included in World Journal of Pharmacy and Pharmaceutical Sciences in 2021.Reference of 3438-16-2 This article mentions the following:

The aim of this work is the detection, identification and elucidation of structure of organic impurity which may present in bulk drugs and pharmaceutical formulations. The control of impurities is currently a critical issue to the healthcare manufacturing Various Regulatory authorities like ICH, USFDA, UK- MHRA and CDSCO are emphasizing on the requirements and the identification of impurities Active Pharmaceutical Ingredients’s (API’s) as well as finished products. International Conference of Harmonisation (ICH) formulated guidelines concerning the control and limit of impurities. In this article we have synthesized iso-Pr impurity of Glibenclamide drug, which is a process related impurity. We have developed a novel method of synthesis of Iso-Pr ester impurity of glibenclamide drug. In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2Reference of 3438-16-2).

5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) belongs to organic chlorides. Organochlorines are organic compounds having multiple chlorine atoms. They were the first synthetic pesticides that were used in agriculture. They are resistant to most microbial and chemical degradations. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.Reference of 3438-16-2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

GC-MS comparison of the behavior of chlorine and sodium hypochlorite towards organic compounds dissolved in water was written by Lebedev, Albert T.;Shaydullina, Gulnara M.;Sinikova, Natalia A.;Harchevnikova, Nina V.. And the article was included in Water Research in 2004.Computed Properties of C8H7ClO3 This article mentions the following:

The reaction pathways of aqueous chlorination of anisole, ethylbenzene and o-methoxybenzoic acid being structural fragments of humic matter were studied using gas chromatog.-mass spectrometry. Cl and Na hypochlorite were used as commonly used disinfecting agents. Comparison of the chlorinating agents was performed in terms of the assortment and relative amounts of reaction products. Detailed schemes of the selected substrates transformation were proposed. Quantum chem. calculations were applied to propose structures of the reacting particles and a numerical parameter to estimate an extent of conversion of aromatic substrates during chlorination. In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2Computed Properties of C8H7ClO3).

5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) belongs to organic chlorides. Chlorination modifies the physical properties of hydrocarbons in several ways. These compounds are typically denser than water due to the higher atomic weight of chlorine versus hydrogen. Aliphatic organochlorides are often alkylating agents as chlorine can act as a leaving group, which can result in cellular damage.Computed Properties of C8H7ClO3

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Structural Insights of Benzenesulfonamide Analogues as NLRP3 Inflammasome Inhibitors: Design, Synthesis, and Biological Characterization was written by Fulp, Jacob;He, Liu;Toldo, Stefano;Jiang, Yuqi;Boice, Ashley;Guo, Chunqing;Li, Xia;Rolfe, Andrew;Sun, Dong;Abbate, Antonio;Wang, Xiang-Yang;Zhang, Shijun. And the article was included in Journal of Medicinal Chemistry in 2018.COA of Formula: C8H7ClO3 This article mentions the following:

NLRP3 inflammasome plays critical roles in a variety of human diseases and represents a promising drug target. In this study, we established the in vivo functional activities of JC124, a previously identified NLRP3 inflammasome inhibitor from our group, in mouse models of Alzheimer’s disease and acute myocardial infarction. To understand the chem. space of this lead structure, a series of analogs were designed, synthesized, and biol. characterized. The results revealed the critical roles of the two substituents on the benzamide moiety of JC124. On the other hand, modifications on the sulfonamide moiety of JC124 are well tolerated. Two new lead compounds, 14 and 17, were identified with improved inhibitory potency (IC₅₀ values of 0.55 ± 0.091 and 0.42 ± 0.080 μM, resp.). Further characterization confirmed their selectivity and in vivo target engagement. Collectively, the results strongly encourage further development of more potent analogs based on this chem. scaffold. In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2COA of Formula: C8H7ClO3).

5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) belongs to organic chlorides. Organochlorines stimulate the central nervous system and cause convulsions, tremor, nausea, and mental confusion. Examples are dichlorodiphenyltrichloroethane (DDT), chlordane, lindane, endosulfan, and dieldrin. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control.COA of Formula: C8H7ClO3

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Design and Performance Validation of a Conductively Heated Sealed-Vessel Reactor for Organic Synthesis was written by Obermayer, David;Znidar, Desiree;Glotz, Gabriel;Stadler, Alexander;Dallinger, Doris;Kappe, C. Oliver. And the article was included in Journal of Organic Chemistry in 2016.SDS of cas: 3438-16-2 This article mentions the following:

A newly designed robust and safe laboratory scale reactor for syntheses under sealed-vessel conditions at 250° maximum temperature and 20 bar maximum pressure is presented. The reactor uses conductive heating of a sealed glass vessel via a stainless steel heating jacket and implements both online temperature and pressure monitoring in addition to magnetic stirring. Reactions are performed in 10 mL borosilicate vials that are sealed with a silicone cap and Teflon septum and allow syntheses to be performed on a 2-6 mL scale. This conductively heated reactor is compared to a standard single-mode sealed-vessel microwave instrument with respect to heating and cooling performance, stirring efficiency, and temperature and pressure control. Importantly, comparison of the reaction outcome for a number of different synthetic transformations performed side by side in the new device and a standard microwave reactor suggest that results obtained using microwave conditions can be readily mimicked in the operationally much simpler and smaller conventionally heated device. In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2SDS of cas: 3438-16-2).

5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) belongs to organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. Organochlorine compounds are lipophylic, meaning they are more soluble in fat than in water. This gives them a high tenancy to accumulate in the food chain (biomagnification).SDS of cas: 3438-16-2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Structural modifications of benzanilide derivatives, effective potassium channel openers. X. was written by Calderone, Vincenzo;Coi, Alessio;Fiamingo, Francesca Lidia;Giorgi, Irene;Leonardi, Michele;Livi, Oreste;Martelli, Alma;Martinotti, Enrica. And the article was included in European Journal of Medicinal Chemistry in 2006.Computed Properties of C8H7ClO3 This article mentions the following:

Large-conductance calcium-activated potassium (BK) channels are involved in many fundamental cell functions. Consistently, the ability to activate BK channels by exogenous compounds is considered as a promising pharmacodynamic pattern for the potential treatment of several pathologies. In this perspective, the development of new and selective BK-openers can be considered as an actual field of research. This paper reports the synthesis and pharmacol. evaluation of new benzanilides, useful for deepening the comprehension of the structure-activity relationships, emerged in previous studies on this class of BK-activators. From a structural point of view, these benzanilides belong to a general class of BK-activators, showing a common pharmacophoric model, consisting of two aryl groups linked through an appropriate “spacer” and the almost obligatory presence of a phenolic hydroxyl. In particular, a new series of benzanilides, in which the Ph rings have been widely changed both on the acidic portion and the basic one of the amide spacer, were synthesized. Their vasorelaxing effects, induced through the activation of BK channels, were also evaluated. Although many compounds exhibited effects which could not be attributed to the activation of BK channels, two derivatives showed a clear profile of BK-activators with vasodilator activity comparable to or slightly lower than that recorded for the reference benzimidazolone NS1619. A further mol. modeling approach allowed us to obtain a mol. electrostatic potential feature which suggests a suitable interaction with the receptor site of the BK channel, from a tri-dimensional point of view. This approach seems to represent a further contribution for the development of new BK-activators, designed on the basis of the pharmacophoric model above-mentioned. In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2Computed Properties of C8H7ClO3).

5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Computed Properties of C8H7ClO3

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some interconversion reactions of organolithium compounds was written by Gilman, Henry;Langham, Wright;Moore, Fred W.. And the article was included in Journal of the American Chemical Society in 1940.Product Details of 3438-16-2 This article mentions the following:

Details are given of 28 reactions of halo derivatives of C₆H₆, PhMe and PhOMe with BuLi in ether or petr. ether (I) with carbonation by pouring upon solid CO₂ to give acids. PhBr in ether (0.25-0.5 h.) gives 46-51% of BzOH; reaction of 0.05 mol. mixture for 1, 5, 20 and 24 h. gives 36, 15, trace and 3.4% BzOH; in I (24 h.) the yield of BzOH is 44.8%. PhI (0.25 h.) gives 49-51% BzOH; after 0.5 and 1 h. the yields are 41 and 27%; in 5 and 20 h. the yields are 13% and a trace. m-ClC₆H₄I gives 41.5% of m-ClC₆H₄CO₂H. p-ClC₆H₄Br gives 90% of p-ClC₆H₄CO₂H. p-C₆H₄B₂ in ether gives 54% p-BrC₆H₄CO₂H; in I (24 h.), 88.7% of p-C₆H₄(CO₂H)₂; in ether (5.5 h.) there was formed 67% of p-BrC₆H₄CO₂H and 33% of p-C₆H₄(CO₂H)₂. 1,3,5-C₆H₃Br₃ gives 71% of 3,5-Br₂C₆H₃CO₂H. o-BrC₆H₄Me in ether (0.25 h.) gives 83.8% and in I (20 h.) 41.7% o-MeC₆H₄CO₂H. m-BrC₆H₄Me in ether (0.25 h.) gives 65.4% and in I (20 h.) 46.1% of m-MeC₆H₄CO₂H. p-BrC₆H₄Me in ether gives 51% and in I 86.2% of p-MeC₆H₄CO₂H. p-IC₆H₄Me in ether yields 72% p-MeC₆H₄CO₂H. o- and p-BrC₆H₄OMe give 72.3 and 52% of o- and p-MeOC₆H₄CO₂H; p-IC₆H₄OMe gives 78% of p-MeOC₆H₄CO₂H. 2,5-Br₂C₆H₃Me (II) and BuLi (0.025 mol each) (15 min.) give 63% of a mixture containing 29% of 3,4-MeBrC₆H₃CO₂H (III), 20.5% of the 2,4-isomer (?) (IV) and 19% of II; with 0.025 mol of II and 0.03 mol BuLi (2 min.) there results 36.1% III and 22.3% IV; in I 0.015 mol II and 0.033 mol BuLi after 20 h. give 12.4% of III and 51.8% of 3-MeC₆H₃-(CO₂H)₂-1,4 (V); 0.01 mol II and 0.04 mol BuLi give 64.4% of V. 3-Bromoacenaphthene gives 55-62% of 3-acenaphthoic acid. (4-BrC₆H₄)₂ in 1 experiment gave 65% p-BrC₆H₄C₆H₄CO₂H (VI); in a 2nd experiment there was formed 67% of VI and 30% of (p-HO₂CC₆H₄)₂ (VII); in I the yield is 13% VI and 60.6% VII; in an experiment in which the I was distilled off during 10 h. the yield of VII was 91%. PhCH:CHBr and BuLi, heated in I for 20 h., give 23% of trans-PhCH:CHCO₂H; after 1 h., the yield is 19%; in ether there is formed 42.5% of PhCCCO₂H. p-ClC₆H₄OMe in ether gives 56% of 5,2-Cl(MeO)C₆H₃CO₂H, m. 97.5° (previously reported 80-2°); after 24 h. at 18-20° the yield was 74%. p-FC₆H₄OMe gives 10-13% of 5,2-F(MeO)C₆H₃CO₂H. 2,4,6-Br₃C₆H₂OMe in ether gives 16-19% of 3,5,2-Br₂(MeO)C₆H₂CO₂H; in I there results 75-88% of 5,2,1,3-Br(MeO)C₆H₂(CO₂H)₂. p-BrC₆H₄OPh gives 70% of p-PhOC₆H₄CO₂H. (4-BrC₆H₄)₂O yields 56.3% of 4-(4-BrC₆H₄O)C₆H₄CO₂H. Procedures are given for the conversion of small blocks of Li to the generally more effective smaller particles. An apparatus is illustrated for filtration of organolithium solutions Advantages of the use of I as a solvent in this type of reaction are listed. The following generalizations are drawn from this work: Metalation of aryl ethers involves H or hydrogens on C ortho to the ether linkage. All types of aryl bromides and iodides undergo the halogen-metal interconversion reaction. Iodides react more readily than the bromides, and chlorides and fluorides are essentially not affected. There are 2 chief competitive reactions: halogen-metal interconversions (RX + R’Li → RLi + R’X) and couplings (RX + R’Li → RLi + R’X → RR’ + LiX). The coupling reaction is not only the slower reaction but often also follows the interconversion reaction. As the reaction time is extended, the coupling reaction predominates and eventuates in the essential disappearance of RLi compound In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2Product Details of 3438-16-2).

5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) belongs to organic chlorides. Organic chlorides can cause corrosion in pipelines, valves and condensers, and cause catalyst poisoning. The hydrocarbon processing industry (HPI) and others are affected by damage caused by these substances. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.Product Details of 3438-16-2

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Metalation and halogen-metal interconversion reactions of some halogenated phenyl ethers was written by Langham, Wright;Brewster, R. Q.;Gilman, Henry. And the article was included in Journal of the American Chemical Society in 1941.Electric Literature of C8H7ClO3 This article mentions the following:

The reactions of certain halogen derivatives of Ph₂O with MeLi, BuLi and PhLi have been studied. When the halogen is I or Br, halogen-metal interconversion is found to be the predominant reaction. IC₆H₄OPh undergo interconversion more readily than the Br derivatives and the Cl derivatives are essentially not affected. During long periods of reaction or upon refluxing in ether, p-Br and p-Cl derivatives are metalated by MeLi, BuLi and PhLi; under the same conditions the p-I derivative is metalated in reactions with BuLi and PhLi. In general 0.01 mol of the ether was reacted with 0.02 mol of the Li derivative at 26° for 0.25 h. 2-IC₆H₄OPh with BuLi gives 79%, PhLi 56% (79% at 18-20° for 24 h.), MeLi (0.1 mol) 14% of 2-PhOC₆H₄CO₂H after carbonation of the reaction product. 3-IC₆H₄OPh with BuLi gives 75% or with 0.1 mol PhLi 37% of 3-PhOC₆H₄CO₂H. 4-IC₆H₄OPh (I) with BuLi gives 93% or 0.1 mol of PhLi gives 33% of 4-PhOC₆H₄CO₂H; 0.02 mol I and 0.1 mol of BuLi at 20-2° for 26 h. or 0.02 mol I and 0.02 mol of PhLi at 34° for 15 h. give 30 or 32% of 2,5-(PhO)-IC₆H₃CO₂H. 4-IC₆H₄OC₆H₄OMe-4 with 0.2 mol BuLi or 0.01 mol of PhLi gives 61 or 47% of 4-(4′-MeOC₆H₄O)-C₆H₄CO₂H. 2-BrC₆H₄OPh and BuLi give 65% of 2-PhOC₆H₄CO₂H. 4-BrC₆H₄OPh with 0.01 mol of BuLi for 0.033 h. or 0.02 mol of PrLi at 26° for 0.083 h. gives 36 or 80% of 4-PhOC₆H₄CO₂H; 0.1 mol of PhLi gives 7% of 2,5-(PhO)BrC₆H₃CO₂H; 0.15 mol ether and 0.8 mol PhLi at 20° for 24 h. or 0.01 mol of ether and 0.01 mol of MeLi for 24 h. at 20° give 35 and 14% of 2,5-(PhO)-BrC₆H₃CO₂H. 3,4-Br(MeO)C₆H₃OPh gives with BuLi 66% of 2,5-MeO(PhO)C₆H₃CO₂H. 2-ClC₆H₄OPh does not react with MeLi at 20° after 24 h. 2,5-(PhO)ClC₆H₃CO₂H results in 16, 23, 36 and 14% yields from 0.005, 0.015, 0.02 or 0.01 mol of 4-ClC₆H₄OPh with 0.008 mol BuLi at 26° in 0.25 h., 0.02 mol BuLi at 34° in 10 h., 0.01 mol of PhLi at 20° in 26 h. or 0.01 mol of MeLi at 20° in 24 h. Many comments are given on the individual experiments p-FC₆H₄OMe (0.03 mol) and 0.05 mol MeLi (all experiments at 34° for 14 h.) give 17.7% of 2,5-(MeO)FC₆H₃CO₂H and 38.5% unreacted F compound p-ClC₆H₄OMe (0.03 mol) gives 21.6% of 2,5-(MeO)ClC₆H₃CO₂H and 57% unreacted Cl derivative p-BrC₆H₄OMe (0.02 mol) and 0.03 mol MeLi give 21.7% of 2,5-(MeO)BrC₆H₃CO₂H; in another experiment there resulted 16% of acid and 50% of unreacted Br compound p-IC₆H₄OMe (0.03 mol) and 0.05 mol of MeLi give 13.1% of 4-MeOC₆H₄CO₂H and 48.6% of p-MeC₆H₄OMe; in a 2nd experiment the yields were 5 and 52%, resp. o-ClC₆H₄OMe does not react with MeLi. o-BrC₆H₄OMe gives 16.6% of 2-MeOC₆H₄CO₂H and 43.5% of o-MeC₆H₄OMe. o-IC₆H₄OMe (0.013 mol) and 0.03 mol of MeLi give 12.5% of 2-MeOC₆H₄CO₂H and 75% of o-MeC₆H₄OMe. m-BrC₆H₄OMe (0.02 mol) and 0.03 mol of MeLi give 0.7 g. of an acidic gum, 13% of m-MeC₆H₄OMe and 0.43 g. of a product b₉ 79-81°. In the experiment, the researchers used many compounds, for example, 5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2Electric Literature of C8H7ClO3).

5-Chloro-2-methoxybenzoic acid (cas: 3438-16-2) belongs to organic chlorides. Organochlorines are organic compounds having multiple chlorine atoms. They were the first synthetic pesticides that were used in agriculture. They are resistant to most microbial and chemical degradations. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. However, the extent of chlorination is difficult to control.Electric Literature of C8H7ClO3

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics