N-bromobutanimide → 5-Amino-2-bromo-4-methylbenzoic acid

Participants

Reaction Steps

To a cooled solution (5° C.) of 3-amino-4-methylbenzoic acid (3.02 g, 20 mmol) in DMF (20 mL) was added NBS (3.38 g, 19 mmol) in small portions at such a rate that the reaction mixture temperature was kept below 15° C. After being stirred for one hour, the reaction mixture was poured onto ice water (100 mL) with stirring. The solid formed was collected by filtration, and the filter cake was washed with ice water (3×100 mL) and then dried at 60° C. under high vacuum to give 5-amino-2-bromo-4-methylbenzoic acid (3.55 g, yield 77.5%) as a pink solid. MS: m/z=230.0 (M+1, ESI+).

Provenance & Evidence