Ammonium Chloride → 4-Amino-2-chloro-5-fluorophenol

Participants

Reaction Steps

Zinc dust (10 g, 160 mmol) was added portion wise to a solution of 2-chloro-5-fluoro-4-nitro-phenol (3.0 g, 16 mmol) and NH4Cl (8.4 g, 160 mmol) in THF (150 mL) and MeOH (150 mL) and the mixture was stirred at RT for 0.5 h. The reaction mixture was filtered, and the filter cake was washed with EtOAc (3×50 mL). The combined filtrate was washed with brine (3×100 mL), dried over Na2SO4 and concentrated to provide 4-amino-2-chloro-5-fluorophenol (2.5 g, 100% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.39 (s, 1 H), 6.76 (d, J=9.2 Hz, 1 H), 6.65 (d, J=12.4 Hz, 1 H), 4.70 (s, 2 H).

Provenance & Evidence