3-Nitrobenzoic acid → 3-Bromo-5-nitrobenzoic acid

Participants

Reaction Steps

A solution of 3-nitrobenzoic acid (16.7 g, 100 mmol) in trifluoroacetic acid (50 mL) and sulfuric acid (20 mL) was stirred at 50° C., and N-bromosuccinimide (26.7 g, 150 mmol) was added in three portions over 3 hours. The mixture was stirred for 16 hours and then cooled to room temperature. The mixture was then poured into ice water (200 mL) and extracted three times with ethyl acetate. The organic layers were combined, dried over sodium sulfate and concentrated under vacuum. The residue was recrystallized from dichloromethane to provide a white solid (17.7 g, 72%). 1H NMR (300 MHz, DMSO-d6) δ13.8 (bs, 1H), 8.60 (s, 1H), 8.55 (s, 1H), 8.37 (s, 1H).

Provenance & Evidence