Hydrochloric Acid → 3-Bromo-4-carbamoylbenzoic acid

Participants

Reaction Steps

Methyl 3-bromo-4-(aminocarbonyl)benzoate (0.54 mmol) was dissolved in methanol (1 mL) and was treated with 1M aqueous sodium hydroxide (1 mL) at 45° C. for 3 h. The reaction mixture was cooled to room temperature and concentrated to afford an aqueous residue that was acidified with 1N aqueous hydrochloric acid to pH ˜3. The precipitate was collected by filtration, washed with water, and dried to afford 3-bromo-4-(aminocarbonyl)benzoic acid (69.4 mg, 0.28 mmol, 53% overall). 1H NMR (400 MHz, d6-DMSO): 13.47 (br s, 1H), 8.08 (dd, 1H), 8.00 (br s, 1H), 7.94 (dd, 1H), 7.73 (br s, 1H), 7.51 (d, 1H); MS (EI) for C8H6BrNO3: 242, 244(M−H).

Provenance & Evidence