Ammonium Chloride → 2-Amino-4-bromo-5-(trifluoromethyl)phenol

Participants

Reaction Steps

To a mixture of zinc powder (16.23 g, 248 mmol) and ammonium chloride (13.28 g, 248 mmol) in MeOH (80 mL) was added 4-bromo-2-nitro-5-(trifluoromethyl)phenol (7.1 g, 24.8 mmol) and the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was partitioned between EtOAc (100 mL) and water (300 mL). The organic phase was separated and washed with brine (30 mL), dried over Na2SO4, filtered and concentrated in vacuo to give 2-amino-4-bromo-5-(trifluoromethyl)phenol as a black oil (5.9 g, 93%), which was used in the next step without further purification. 1H NMR (DMSO-d6, 400 MHz): δ 9.89 (brs 1H), 6.98 (s, 1H), 6.92 (s, 1H), 5.53 (brs, 2H).

Provenance & Evidence