2-Bromobenzoic acid → 2-bromo-N-(4-nitrophenyl)benzamide

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (120.5 g) was added to a stirred mixture of 2-bromobenzoic acid (194.0 g) in toluene (500 mL) and N,N-dimethylformamide (DMF) (5 mL) and the mixture heated at 80° C. for 4 hours. The solution was cooled to 20° C. and added slowly to a solution of 4-nitroaniline (133.1 g) in toluene (500 mL) and N-methylpyrrolidone (NMP) (120 mL), maintaining the temperature of the reaction mixture between 20°-25° C. The reaction mixture was then stirred for 24 hours, during which time a solid precipitated. Water (360 mL) was added with rigorous stirring. The suspended solid was collected by filtration, and washed successively with water, toluene and acetonitrile to give 2-bromo-N-(4-nitrophenyl)benzamide (B) as a solid, in 87% yield; m.p. 200°-202° C.; NMR (d6 -DMSO): 7.4-7.8(m, 7H), 8.0(d, 2H), 8.3(d, 2H), 11.5(br s, 1H). This material was used without further purification in step (ii).

Provenance & Evidence