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Discovery of 54932-72-8

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.

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. 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, A new synthetic method of this compound is introduced below., name: 4-Bromo-1-chloro-2-methylbenzene

A mixture of 3-(3-chlorophenyl)-1H-pyrazole (5.3 g, 29.8 mmol) (prepared according to the method given in European Patent Publication EP 538156), salicylaldoxime (0.58 g, 4.25 mmol), 5-bromo-2-chlorotoluene (2.8 g, 21.3 mmol), copper oxide (0.15 g, 1.06 mmol) and cesium carbonate (11.8 g, 36.2 mmol) in 20 mL of Af N-dimethylformamide was heated at 140 C overnight and then allowed to cool to room temperature. The resulting suspension was filtered and the filtrate was concentrated under reduce pressure. The resulting residue was purified by medium pressure liquid chromatography (2 to 10% gradient of ethyl acetate in hexanes as eluant) to give the title compound as a white solid (1.4 g). 1H NMR (CDCl3): 5 7.92-7.30 (m, 8H), 6.78 (s, 1H), 2.46 (s, 3H)

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2008/124092; (2008); A2;,
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Introduction of a new synthetic route about 54932-72-8

To a stirring solution of 4-bromo-1-chloro-2-methyl-benzene 5 (4.92mL, 37.1mmol) in THF (75mL) cooled to -78C was added n-butyllithium (14.9mL, 37.1mmol) dropwise. The solution was stirred at -78C for 30min and then was added to a stirring solution of phthalic anhydride 6 (5.00g, 33.8mmol) in THF (90mL) at -78C. The reaction was stirred at -78C for 2h before being quenched with 1N HCl (100mL). The solution was allowed to warm to rt, the layers were separated and the aqueous layer was extracted with EtOAc (3¡Á100mL). The combined organic layers were passed through a phase separator and concentrated. The crude material was purified using Teledyne ISCO Combi-Flash system (solid loading, 40G column, 40-80% EtOAc, 20min run) to give 2-(4-chloro-3-methyl-benzoyl)benzoic acid 7 (4.67g, 50.4% yield) as a white solid. 1H NMR (400MHz, CDCl3) delta (ppm): 8.10 (d, J=7.8Hz, 1H), 7.68 (dt, J=7.6, 1.2Hz, 1H), 7.64-7.62 (m, 1H), 7.59 (dt, J=7.9, 1.2Hz, 1H), 7.44 (dd, J=8.2, 2.2Hz, 1H), 7

Reference:
Article; McGowan, Kevin M.; Nance, Kellie D.; Cho, Hykeyung P.; Bridges, Thomas M.; Jeffrey Conn; Jones, Carrie K.; Lindsley, Craig W.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 6; (2017); p. 1356 – 1359;,
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Discovery of 54932-72-8

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 54932-72-8.

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. 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H6BrCl

General procedure: Nitrogen was purged through a stirred solution of 4-bromo-1-chloro-2-methylbenzene (258muL, 1.95mmol) in 1,4-dioxane (5mL) for 30min rac-BINAP (363mg, 1.95mmol), caesium carbonate (1.27g, 3.89mmol), 1-Boc-piperazine (363mg, 1.95mmol) and Pd(OAc)2 (87mg, 0.039mumol) and stirred at reflux for 14h under N2. The reaction was filtered through celite and concentrated in vacuo. The residue was dissolved in EtOAc (20mL), filtered through celite and washed with additional EtOAc (50mL). The organic layer was washed with water (2¡Á20mL) and brine (2¡Á20mL), dried with Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography (100% CyHex to 10% EtOAc/CyHex) to obtain the protected intermediate as a solid (413mg, 68%). MS, m/z=255 (100) [M-tBu]. The intermediate was dissolved in a 1:3 mixture of TFA/DCM (4mL) and stirred at 20C for 1h. The solvent was evaporated in vacuo and the crude residue dissolved in EtOAc (10mL) which was successively washed with a 10% solution of NaHCO3 (10mL), water (10mL) and brine (10mL). The organic layer dried with Na2SO4 and concentrated in vacuo to obtain 92 as a solid (211mg, 76%).

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 54932-72-8.

Reference:
Article; Blackmore, Timothy R.; Jacobson, Jonathan; Jarman, Kate E.; Lewin, Sharon R.; Nguyen, William; Purcell, Damian F.; Sabroux, Helene Jousset; Sleebs, Brad E.; European Journal of Medicinal Chemistry; vol. 195; (2020);,
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Simple exploration of 54932-72-8

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A mixture of 7-amino-2,2-dimethyl-2H-l,4-benzoxazin-3(4H)-one (compound obtained in Reference Example 3(1); 150 mg), 5-bromo-2-chlorotoluene (321 mg), copper(I) iodide (37 mg), potassium carbonate (216 mg), N,N’-dimethylethylenediamine (40 muL) and toluene (8 mL) was heated at 110 C overnight under argon atmosphere. After cooling, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (solvent; n-hexane/ethyl acetate = 4/1 -? 1/1) to give 7-amino-4-(4-chloro- 3-methylphenyl)-2,2-dimethyl-2H-l,4-benzoxazin-3(4H)-one (98 mg) as a pale orange powder.MS(APCI) m/z: 317/319 [M+H]+

Reference:
Patent; TANABE SEIYAKU CO., LTD.; WO2007/89034; (2007); A1;,
Chloride – Wikipedia,
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The important role of 4-Bromo-1-chloro-2-methylbenzene

Adding a certain compound to certain chemical reactions, such as: 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, 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 54932-72-8, 54932-72-8

Extended knowledge of 54932-72-8

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, 54932-72-8, other downstream synthetic routes, hurry up and to see.

A common compound: 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 54932-72-8

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a. 4-(4-chloro-3-methylphenyl)-1-methyl-1H-pyrazole A mixture of 2-chloro-5-bromotoluene (305 mg, 1.48 mmol), 1-methylpyrazole-4-boronic acid pinacol ester (315 mg, 1.51 mmol), Pd(dppf)Cl2 (130 mg, 0.16 mmol), and K2CO3 (400 mg, 2.89 mmol) in a mixture of THF (4 mL) and water (1.2 mL) was heated at 120 C. for 1 h under microwave irradiation. The reaction mixture was concentrated in vacuo and purified by Biotage (SNAP 25 g column, cyclohexane/EtOAc 90/10->50/50) to give the title compound as a brown oil (215 mg, 70%).

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:
Patent; Merck Patent GmbH; Cancer Research Technology, Ltd.; SCHIEMANN, Kai; BLAGG, Julian; MALLINGER, Aurelie; RINK, Christian; SEJBERG, Jimmy; HONEY, Mark; (139 pag.)US2016/16951; (2016); A1;,
Chloride – Wikipedia,
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The important role of 54932-72-8

Nitrogen gas was purged through a stirred solution of 5-bromo-2-chiorotoluene (452 muIota, 3.41 mmol) in 1 ,4-dioxane (15 ml) for 30 mins. 2,2′-Bis(diphenylphosphino)-1 , 1 ‘- binaphthyl (212 mg, 0.34 mmol), Pd(OAc)2 (153 mg, 0.68 mmol) and Cs2C03 (2.22 g, 6.81 mmol) were then added. The stirred solution was then purged of nitrogen for a further 30 min after which 1-Boc-3-aminopyrrolidine (745 muIota, 4.09 mmol) was added and solution stirred at reflux for 48 h under N2. The solvent was then evaporated in vacuo and the crude residue dissolved in EtOAc (40 ml) which was then washed with water (2 x 30 ml), brine (2 chi 30 ml), dried with Na2S04, filtered and concentrated. The crude residue was then purified by column chromatography (100% CyHex to 10% EtOAc/CyHex) to obtain WIN-321 -142-01 as a solid (111 mg, 10.4%).1H NMR (CDCI3): delta 7.13 (d, J 8.4 Hz, 1H), 6.48 (d, J 2.6 Hz, 1H), 6.39 (dd, J 8.58, 2.86 Hz, 1H), 3.99 (br. s., 1H), 3.79-3.57 (m, 2H), 3.56-3.38 (m, 2H), 3.31 -3.14 (m, 1H), 2.30 (s, 3H), 2.10 – 2.26 (m, 1 H), 1.96 – 1.79 (m, 1 H), 1.47 (s, 9H). MS, m/z = 255 (100) [M-56], 257 (30).

Reference:
Patent; THE UNIVERSITY OF MELBOURNE; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; SLEEBS, Brad; PURCELL, Damian Francis John; JACOBSON, Jonathan; LEWIN, Sharon; NGUYEN, William; (163 pag.)WO2017/219083; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

New learning discoveries about 54932-72-8

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-1-chloro-2-methylbenzene. I believe this compound will play a more active role in future production and life.

54932-72-8, The chemical industry reduces the impact on the environment during synthesis 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, I believe this compound will play a more active role in future production and life.

To a solution of 4-bromo-1 -chloro-2-methyl-benzene (30 g, 146 mmol) and benzoyl peroxide (0.71 g, 3 mmol) in acetonitrile (70 mL) was added N-bromosuccinimide (28.6 g, 161 mmol) at 90C and the mixture was stirred overnight. The solution was evaporated under reduced pressure and the crude material was purified onsilica gel to give 4-bromo-2-(bromomethyl)-1 – chloro-benzene as a white solid (40.3 g, 95% yield).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-1-chloro-2-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BASF SE; WINTER, Christian; RHEINHEIMER, Joachim; WOLF, Antje; POONOTH, Manojkumar; TERTERYAN, Violeta; WIEBE, Christine; KREMZOW-GRAW, Doris; ROeHL, Franz; GRAMMENOS, Wassilios; ROHRER, Sebastian Georgios; WIEJA, Andy; ROSENBAUM, Claudia; WO2014/207052; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics