Nitric Acid → 4-Bromo-5-fluoro-2-nitrophenol

Participants

Reaction Steps

To a 0° C. mixture of 4-bromo-3-fluorophenol (70.0 g, 366 mmol) in DCM (500 mL) was added HNO3 (23.0 g, 366 mmol) carefully and the reaction mixture was stirred 30 min. The reaction mixture was poured into water (1 L) and extracted with DCM (3×500 mL). The combined organic portion was washed with brine (300 mL) and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was crystallized from EtOH to give 4-bromo-5-fluoro-2-nitrophenol (42.0 g, 49%). 1H NMR (DMSO-d6, 400 MHz): δ 11.72 (brs, 1H), δ 8.30 (d, J=7.2 Hz, 1H), 7.09 (d, J=10.0 Hz, 1H).

Provenance & Evidence