Month: December 2020

50638-47-6, These common heterocyclic compound, 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene, 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.

To a magnetically stirring solution of 4-bromo-2-chloroanisole (0.50 g, 2.61 mmol) and 1-Cyclopentyl-2-propen-1-ol (1.5 eq, 0.49 g, 3.88 mmol) in anhydrous N-methylpyrrolidinone (3.0 mL), under argon at room temperature, was added sodium bicarbonate (1.2 eq, 0.26 g, 3.10 mmol) followed by dichlorobis (triphenylphosphine) palladium (II) (0.02 eq, 36.7 mg, 0.05 mmol). The resulting mixture was heated to 140 C. in an oil bath and maintained for 4 hours. The resulting dark reaction mixture was cooled to room temperature and poured into water (50 mL) and extracted with EtOAc (2¡Á25 mL). The organics were washed with water (50 mL) and brine (50 mL) then dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash chromatography (1% through 10% EtOAc in Hexanes) to yield the intermediate ketone as a slightly yellow oil (0.49 g, 79%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 50638-47-6.

Reference:
Patent; Agouron Pharmaceuticals, Inc.; US2005/176701; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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.

To a solution of 2,4-Dichloro-1-fluorobenzene (165.0 g, 1.0 mol) in THF (500 mL) n-BuLi (420 mL, 2.5 M, 1.05 mol) was added at -78 C. After stirring at -78 C for 1 h, Oxirane (44.0 g, 1.0 mmol) was added and stirred at -78 C for 2 h. The mixture was quenched with sat. NH4Cl solution, extracted with EtOAc (200 mL * 3). The organic phase was washed with water (100 mL * 2), brine (100 mL * 2), dried over Na2SO4. After filtering, the organic phase was concentrated to give compound 44 as a colorless liquid (156.7 g, 75.0% yield). 1H NMR (400 MHz, CDCl3) delta 7.29-7.25 (m, 1H, Ar-H), 7.02-6.97 (m, 1H, Ar-H), 3.89-3.84 (m, 2H, CH2), 3.29-3.24 (m, 2H, CH2).

The synthetic route of 2,4-Dichloro-1-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Na; Wang, Yanfen; Huang, Gongchao; Ji, Conghui; Fan, Wei; Li, Haitao; Cheng, Ying; Tian, Hongqi; Bioorganic Chemistry; vol. 65; (2016); p. 146 – 158;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., 3972-56-3

General procedure: An oven-dried Schlenk tube was evacuated and backfilled with nitrogen. The Schlenk tube was charged with Pd(bda)2 (11.5 mg,0.02 mmol), L1 (13.7 mg, 0.03 mmol), K3PO4 (424.5 mg, 2 mmol), and toluene (1.0 mL). After stirring for 15 min, the solution of arylhalide (1.0 mmol) and phenol (1.2 mmol) in toluene (1.5 mL) was added. The septum was replaced with an inside reflux condenser, and then the reaction mixture was stirred for 18 h at 110 C. Then,the reaction mixture was cooled to room temperature and quenched with water (5 mL). After separating the organic phase, the aqueous phase was extracted with ethyl acetate (3 mL3), and the combined organic phase was dried over anhydrous Na2SO4. The solvent was concentrated under reduced pressure, and then the crude material was purified by column chromatography on silica gel

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Zhang, Yi; Ni, Gang; Li, Chengjun; Xu, Sheng; Zhang, Zhaoguo; Xie, Xiaomin; Tetrahedron; vol. 71; 30; (2015); p. 4927 – 4932;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

106131-61-7, The chemical industry reduces the impact on the environment during synthesis 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, I believe this compound will play a more active role in future production and life.

General procedure: Dichloro-s-tetrazine (1 mmol) and fluorinated alcohol (1 mmol) were dissolved in anhydrous dichloromethane (10 mL). 2,4,6-collidine (1 mmol) was added dropwise at room temperature in the solution, and the mixture was stirred for 12 h under N2 atmosphere.The solvent was evaporated and the residue was passed through a column of silica (2/8 dichloromethane/petroleum ether v/v) to give compound 2 as a pink solid, with a ?yellow? fluorescence on TLC (using a standard laboratory UV lamp with a broad band centred at 365 nm).

The chemical industry reduces the impact on the environment during synthesis 3,6-Dichloro-1,2,4,5-tetrazine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ben Chaabane, Radhia; Guermazi, Refka; Clavier, Gilles; Audebert, Pierre; Hedhli, Ahmed; Dyes and Pigments; vol. 108; (2014); p. 64 – 69;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6276-54-6, 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. 6276-54-6 name is 3-Chloropropan-1-amine hydrochloride, 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.

di-tert-butyl dicarbonate(10.89 g, 50mmol)was dissolved in 50 ml THF. The solutionwas cooledto 0 C. 3-Chloropropan-1-amine hydrochloride (6.46 g, 69 mmol) wasdissolved in 20 ml of 1 M NaOH solution and added using a droppingfunnel, and the solution was stirred overnight. 150 ml of ethyl acetatewere added and extraction was performed. The organic phase waswashed three times with water and once with brine, and then driedover magnesium sulfate. The solvent was removed and a viscous oilwas produced, which was dried under vacuum (7.27 g, 68%). 1H NMR(400 MHz, CDCl3) delta (ppm): 4.80 (bs, NH), 3.53 (t, J = 6.4 Hz, 2H),3.22 (q, J = 6.4 Hz, 2H), 1.91 (quin, J = 6.4 Hz, 2H),1.42 (s, 9 H). 13CNMR (100 MHz, CDCl3, delta, ppm): 156, 79, 42, 37, 32, 28.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloropropan-1-amine hydrochloride, and friends who are interested can also refer to it.

Reference:
Article; Weiss, Ester; Gertopski, Diana; Gupta, Maneesh Kumar; Abu-Reziq, Raed; Reactive and functional polymers; vol. 96; (2015); p. 32 – 38;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

72934-36-2, 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. 72934-36-2 name is 1-(4-Chlorophenyl)cyclopropanamine, 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 slurry of tert-butyl 4-(4-chloro-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate (3.6 g) and 1-(4-chlorophenyl)cyclopropanamine (1.49 g) in THF (50 mL) was stirred for 5 hours at 80 C. The precipitate was filtrated through a plug washing with THF to give a crude product that was purified by Biotage eluting with 4/1-hexane/ethyl acetate to give 1.8 g of tert-butyl 4-(4-(1-(4-chlorophenyl)cyclopropylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylamino)benzoate as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(4-Chlorophenyl)cyclopropanamine, and friends who are interested can also refer to it.

Reference:
Patent; WANG, TAO; Yin, Zhiwei; Scola, Paul Michael; US2014/135335; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

73006-78-7, The chemical industry reduces the impact on the environment during synthesis 73006-78-7, name is 5-Chloro-[1,1′-biphenyl]-2-amine, I believe this compound will play a more active role in future production and life.

A mixture of the product from step (i) (0.94g), sodium acetate (0.5g) and tert- butylbromoacetate (0.6ml) in ethanol (20ml) was heated under reflux for 5h. A further porton of sodium acetate (Ig) and tert-butylbromoacetate( 1.2ml) was added and the mixture heated under reflux overnight. The solvent was evaporated under reduced pressure and the residue partitioned between ethyl acetate and water, the organic layer was washed with water, dried, and the solvent evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5% ethyl acetate/isohexane, yield 0.775g. MS: APCI (-ve) 260 (M-l-tBu)

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-[1,1′-biphenyl]-2-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/37982; (2006); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

19752-55-7, A common heterocyclic compound, 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, molecular formula is C6H3BrCl2, 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.

Step 3 : 2-(1-((5-chlorobenzo[b]thiophen-3-yl)methyl)-6-(3,5-dichlorophenyl)-1H-indol-3- yl)acetic acid (733); [0635] To a solution of 2-(l-((5-chlorobenzo[b]thiophen-3-yl)methyl)-6-(5,5- dimethyl-l,3,2-dioxaborinan-2-yl)-lH-indol-3-yl)acetic acid (44.1 mg, 0.09428 mmol) and 1- bromo-3,5-dichlorobenzene (21.30 mg, 0.09428 mmol) in toluene (2 mL) was added Na2COs (0.2357 ml, 0.4714 mmol) and Pd(PPh3)4 (5.447 mg, 0.004714 mmol). To the solution was added 0.5 mL of EtOH to help solubility. After purging under N2, the reaction mixture was heated to 90 ¡ãC overnight.[0636] The reaction was then acidified with 2N HCl and extracted with EtOAc (3x). The combined organics and washed with brine, dried with MgSO4 and concentrated down to light brown-orange solid. This solid was diluted in CH2Cl2 and Et2O and the resulting .solid was collected by filtration to afford 733 (15.8 mg, 33.46percent yield). MS APCI (+) m/z 497.8 detected.

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INTERMUNE, INC.; WO2008/100867; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 38762-41-3, name is 4-Bromo-2-chloroaniline, I believe this compound will play a more active role in future production and life. 38762-41-3

To a solution of 2,3,4-trifluorobenzoic acid (1 g, 5.68 mmol) and 4-bromo- 2-chloroaniline (1.2 g, 5.68 mmol) in acetonitrile (10 mL) was added lithium amide (0.39 g, 17.04 mmol) and the reaction stirred at 60 0C for 1.5 hours. The mixture was cooled to room temperature and then to 0 0C and acidified with aq. hydrochloric acid. The obtained precipitate was collected by filtration and washed with cold water and dried in vacuo to afford 2-[(4-bromo-2-chlorophenyl)amino]-3,4-difluorobenzoic acid (1.92 g, 94% yield) as a beige solid. MS (EI) for C13H7BrClF2NO2: 363 (MH+). [00310] Using the same or analogous synthetic techniques and substituting, as necessary, with alternative reagents, 2-[(4-iodo-2-fluorophenyl)amino]-3- fluorobenzoic acid was prepared. MS (EI) for Ci3HgF2INO2: 376 (MH+).

The chemical industry reduces the impact on the environment during synthesis 38762-41-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; EXELIXIS, INC.; WO2008/76415; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 38762-41-3, name is 4-Bromo-2-chloroaniline, 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 38762-41-3, 38762-41-3

Example 209 Ethanesulfonic acid [5-(8-chloro-l-methyl-2-oxo-l,2,3,4-tetrahydro-quinolin-6-yl)- pyridin-3-ylmethyl] -amide[A] N-(4-Bromo-2-chloro-phenyl)-3-chloro-propionamideTo a solution of 4-bromo-2-chloro-phenylamine (32 g, 0.15 mol) and pyridine (13.45 g, 0.17 mol) in DCM (200 mL) was added 3-chloropropionyl chloride (21.65 g, 0.17 mol) dropwise at 15 C. After stirring at room temperature for 1 hour, the mixture was washed with water and then hydrochloric acid (2 N, aqueous). The organic layer was dried over anhydrous Na2S04, filtered, and concentrated in vacuo to afford title compound (10.9 g, yield: 90%) as a white solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-2-chloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; HORNSPERGER, Benoit; KNUST, Henner; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; ZHOU, Mingwei; WO2013/37779; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics