Month: May 2021

Electric Literature of 93-50-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 93-50-5, name is 4-Chloro-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6,8-dichloro-4-oxo-chromene-2-carboxylic acid (Int-2, 1.3 g, 5.02 mmol) in DCM (20 mL) was added 4-chloro-2-methoxyaniline (949 mg, 6.02 mmol), DIPEA (1.15 g, 8.9 mmol) and HATU (3.3 g, 8.9 mmol) at room temperature and the resulting mixture was then stirred at room temperature for 18 hours. After the reaction was completed, the mixture was diluted with water (30 mL) and extracted with EtOAc (50 mL) three times. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo. The residue was purified by silica gel flash chromatography (elution with PE/EtOAc=lO: 1-1:4) to give 6,8-dichloro-N-(4-chloro-2-methoxyphenyl)-4-oxo-chromene-2-carboxamide (1.6 g, 80 %) as a yellow solid. MS obsd. (ESP) [(M+H)+]: 398.1.

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-2-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; LIANG, Chungen; LIU, Yongfu; TAN, Xuefei; WU, Jun; WANG, Jianping; (134 pag.)WO2020/79106; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1435-48-9, A common heterocyclic compound, 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene, molecular formula is C6H3Cl2F, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Reference Example 2-44 2,4-Dichloro-5-fluorobenzoic acid Following the procedure described in Reference Example 2-25, the title compound was prepared from 2,4-dichloro-1-fluorobenzene (66% yield). NMR (CDCl3) delta: 7.59 (1H, d, J=6.2 Hz), 7.85 (1H, d, J=8.8 Hz), 8.28 (1H, br s).

The synthetic route of 1435-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Uchikawa, Osamu; Mitsui, Keita; Asakawa, Akiko; Morimoto, Shigeru; Yamamoto, Masataka; Kimura, Hiroyuki; Moriya, Takeo; Mizuno, Masahiro; US2003/187014; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 118-69-4, name is 2,6-Dichlorotoluene, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 118-69-4, Computed Properties of C7H6Cl2

EXAMPLE 1-1 Preparation of 2,4-dichloro-3-methylbromobenzene To a solution of 48.8 g (0.3 mol) of 2,6-dichlorotoluene in 60 ml of carbon tetrachloride, 0.7 g of iron powder and 0.1 g of iodine were added. Then, 52.8 g (0.33 mol) of bromine was dropwise added thereto at room temperature while maintaining the reaction temperature at a level of from 22 to 25 C. After completion of the dropwise addition, the reaction was continued at the same temperature until generation of hydrogen bromide ceased. After the reaction, the reaction solution was added to 300 ml of ice water and extracted with 300 ml of 1,2-dichloroethane. The organic layer was separated and washed sequentially with water, a saturated sodium hydrogen sulfite aqueous solution, water and a saturated sodium chloride aqueous solution. Then, the solvent was distilled off under reduced pressure to obtain 71.9 g (yield: 99.5%) of desired 2,4-dichloro-3-methylbromobenzene. Melting point: 32-33 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichlorotoluene, and friends who are interested can also refer to it.

Reference:
Patent; Nissan Chemical Industries Ltd.; US4942246; (1990); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 67279-24-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 67279-24-7 name is 1,4-Dichloro-5,6,7,8-tetrahydrophthalazine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 1,4-dichloro-5,6,7,8-tetrahydro-phthalazine (compound 25, 100 mg, 0.492 mmol) in NMP (3 mL) is added 1-[5-trifluoromethyl)-pyrid-2-yl)-piperazine (114 mg, 0.492 mmol) followed by triethyl amine (218 muL, 1.57 mmol). The mixture was heated in a microwave reactor for 140 C. for 60 min. Water was added to the reaction mixture and extracted with EtOAc. The combined arganic extracts were washed with water, brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (EtOAc/heptane 10% to 70%) to yield 96 mg (49%) of the title compound.1H NMR (400 MHz, CD2Cl2) delta=8.41 (s, 1H), 7.73 (dd, J=9.0 Hz, 2.5 Hz, 1H), 6.79 (d, J=9.0 Hz, 1H), 3.85 (m, 4H), 3.40 (m, 4H), 2.76-2.68 (m, 4H), 1.93 (m, 2H), 1.80 (m, 2H).HR MS (m/z, MH+) meas. 398.1359.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,4-Dichloro-5,6,7,8-tetrahydrophthalazine, and friends who are interested can also refer to it.

Reference:
Patent; Novartis AG; US2010/41663; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 50594-82-6, name is 3,4,5-Trichlorobenzotrifluoride, molecular formula is C7H2Cl3F3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C7H2Cl3F3

Comparative Example 1 : Preparation of 2,6-dichloro-4-(trifluoromethyl) phenylhydrazine of the formula 1-1 from 3,4,5-trichloro- benzotrifluoride in tetrahydrofurane; 10 g (40 mmole) of 3,4,5-trichlorobenzotrifluoride (99.7% purity) were dissolved in 30 g (417 mmole) of tetrahydrofurane. To this solution were added 8 g (160 mmole) of hydrazine hydrate (100%). The resulting mixture was stirred at 500C for 24 hours. Thereafter, an organic phase of 40.7 g was separated. The solution obtained by this separation contained the product 2,6-dichloro-4-(trifluoromethyl)phenylhydrazine in an amount of 0.9 wt-% and the starting material 3,4,5-trichlorobenzotrifluoride in an amount of 27.1 wt-%, meaning that a product yield not higher than 3.7 % was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 50594-82-6, its application will become more common.

Reference:
Patent; BASF SE; WO2008/113661; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

452-66-4, name is 4-Chloro-1-fluoro-2-methylbenzene, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 452-66-4

4-chloro-2-fluorobenzaldehyde and 5-chloro-2-fluorobenzaldehyde were prepared in an analogous manner from 4-chloro-2-fluorotoluene and 5-chloro-2-fluorotoluene respectively (both supplied by Lancaster Synthesis).

The synthetic route of 452-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Wellcome Foundation; The Regents of the University of California; US5502073; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 110407-59-5, name is 2-Chloro-4-fluorobromobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H3BrClF

To a room temperature solution of 1-bromo-4-fluoro-2-chlorobenzene (1.9 g, 0.97 mmol) in DMSO (10 mL) was added sodium ethanethiolate (0.84 g, 1 mmol) and the resulting reaction mixture was heated to 100 C. for 18 hours. The reaction mixture was partitioned between water (20 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous layer was further extracted with EtOAc (3*50 mL). The organic layers were combined and washed with saturated brine solution (20 mL) then dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography eluting with heptane to afford the title compound as a colourless liquid in 70% yield, 1.6 g. 1H NMR (400 MHz, CDCl3): delta ppm 1.31 (s, 3H), 2.95 (q, 2H), 7.04 (d, 1H), 7.38 (s, 1H), 7.50 (d, 1H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Pfizer Limited; Omoto, Kiyoyuki; Owen, Robert McKenzie; Pryde, David Cameron; Watson, Christine Ann Louise; Takeuchi, Mifune; US2014/171435; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 729590-57-2,Some common heterocyclic compound, 729590-57-2, name is 4-(Benzyloxy)-1-bromo-2-chlorobenzene, molecular formula is C13H10BrClO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step-2: Synthesis of 4-(benzyloxy)-l-(but-l-yn-l-yl)-2-chlorobenzene sealed tube/90 “C/12 h To a stirred solution of 4-(benzyloxy)-l-bromo-2-chlorobenzene (13 g, 43.91 mmol) in 130 mL of DMA in a sealed tube, were added copper iodide (0.833 g, 4.39 mmol) and cesium carbonate (28.63 g, 87.83 mmol) at room temperature. This mixture was degassed with three vacuum/N2 cycles, and were added but-l-yn-l-yltrimethylsilane (11 g, 87.83 mmol, Example-16, Step-2) followed by Pd(OAc)2 (1.079 g, 4.39 mmol) and dppf (2.4 g, 4.39 mmol). The pressure tube was sealed and heated at 90 C for 12 h. Upon completion by TLC, the reaction mixture was diluted with water (250 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with water, brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified over 230-400 mesh silica gel column chromatography using 3% EtOAc in n-hexane to afford 4-(benzyloxy)-l-(but-l-yn-l-yl)-2-chlorobenzene (9.4 g, 80%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Benzyloxy)-1-bromo-2-chlorobenzene, its application will become more common.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; (161 pag.)WO2016/196342; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 39226-95-4, name is 2,3-Dichlorobenzylamine, A new synthetic method of this compound is introduced below., SDS of cas: 39226-95-4

Step 3 To a solution of 60-B (0.10 g, 0.33 mmol ) in CH2C12 (3.5 mL) was added (2,3-diehlorophenyl)methanamine (0.12 g, 0.70 mmol), HATU (0.25 g, 0.66 mmol), and N,N-diisopropylethylamine (DIPEA) (0.29 mL, 1.64 mmol). The resulting solution was stirred at room temperature until judged complete by LC/MS. The reaction mixture was diluted with CH2CI2 and washed with I N HCL The aqueous layer was back-extracted with CH2Ci2, and the combined organic layers were dried over Na2S04 and concentrated in vacuo. The crude material was dissolved in hot DMF and allowed to precipitate upon cooling. Filtration provided 60-C. LCMS-ESI+ (m/z): [M+H]+ calculated for C . -I L -CL O i: 462.10; found: 462.14.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; GILEAD SCIENCES, INC.; JIN, Haolun; LAZERWITH, Scott, E.; MARTIN, Teresa, Alejandra, Trejo; BACON, Elizabeth, M.; COTTELL, Jeromy, J.; CAI, Zhenhong, R.; PYUN, Hyung-Jung; MORGANELLI, Philip, Anthony; JI, Mingzhe; TAYLOR, James, G.; CHEN, Xiaowu; MISH, Michael, R.; DESAI, Manoj, C.; WO2014/100323; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, A new synthetic method of this compound is introduced below., COA of Formula: C3H4Cl3NO

Intermediate 25-2 (17.5 g, 97.6 mmol) was dissolved in acetic acid (220 mL). To the resulting mixture methyl 2,2,2-trichloroacetimidate (CAS 2533-69-9) (12.13 mL, 97.6 mmol) was added at once. The resulting mixture was stirred at 50C for 48 h. The mixture was allowed to cool to room temperature and poured onto ice/water solution. The pH was adjusted to pH=5 by addition of sodium carbonate. The resulting mixture was extracted with dichloromethane (3 X 100 mL). The combined organic layers were successively washed with saturated NaHC03, dried over MgS04 and evaporated. The residue was purified by column chromatography using CH2CI2 to CH2Cl2/EtOAc as the eluent to give an oil which solidified on drying in vacuo (23 g, 77%). m/z = 307 (M+H)+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; JANSSEN R&D IRELAND; COOYMANS, Ludwig Paul; DEMIN, Samuel Dominique; HU, Lili; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; TAHRI, Abdellah; VENDEVILLE, Sandrine Marie Helene; WO2012/80449; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics