The origin of a common compound about 27139-97-5

Statistics shows that 27139-97-5 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-4-chloro-1-methylbenzene.

27139-97-5, name is 2-Bromo-4-chloro-1-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. 27139-97-5

To a solution of 2-bromo-4-chloro-l-methylbenzene (25 g, 0.123 mol) in anhydrous THF (150 mL) at -78 0C under N2 was added drop wise a solution of n- BuLi (2.5 M, 49 mL, 1.18 mol). After stirring at -78 0C for 1 h, a solution of tert- butyl 3-(5-chloro-2-methylphenyl)-3-oxopropyl(methyl)carbamate (26 g, 0.104 mol) in anhydrous THF (150 mL) was added drop wise. After addition, the reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was quenched with saturated NH4Cl, extracted three times with ethyl acetate, and dried over Na2SO4. Solvent removal and flash column chromatography afford tert-butyl 3-(5-chloro-2-methylphenyl)-3-oxopropyl(methyl)carbamate (3.3 g, yield 9 percent). 1H NMR (CDCl3, 400 MH2) delta 1.44 (s, 9H), 2.45 (s, 3H), 2.90 (s, 3H), 3.10 (m, 2H), 3.60 (m, 2H), 7.10 (m, 3H).

Statistics shows that 27139-97-5 is playing an increasingly important role. we look forward to future research findings about 2-Bromo-4-chloro-1-methylbenzene.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; WO2008/156816; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics