Methanol → 4-Amino-2-chloro-3-fluorophenol

Participants

Reaction Steps

A 0° C. solution of 2-chloro-3-fluoro-4-nitrophenol (25 g, 130.9 mmol) in 1:1 MeOH and THF (400 mL) was treated with NH4Cl (70 g, 1.3 mol), followed by the portion-wise addition of zinc (83.2 g, 1.3 mol), then warmed to RT and stirred for 2 h. The solids were removed via filtration, the filtrate concentrated to dryness and the residue was dissolved in EtOAc, washed with brine, dried over Na2SO4 and concentrated to afford 4-amino-2-chloro-3-fluorophenol (16 g, 76%). 1H-NMR (400 MHz, DMSO-d6): δ 9.41 (s, 1 H), 6.59-6.51 (m, 2 H), 4.65 (s, 2H); MS (ESI): m/z 162.2 [M+H]+.

Provenance & Evidence