4-Bromo-2-nitrophenol → 2-Amino-4-Bromophenol

Participants

Reaction Steps

To a stirring solution of 4-bromo-2-nitro-phenol (6 g, 27.52 mmol) in MeOH (150 mL) at room temperature was added a suspension of Na2S2O4 (29 g, 165.13 mmol). The mixture was stirred at room temperature for 3 hrs, filtered and concentrated down. The residue was partitioned between EtOAc and water. The organic layer was collected and dried over Na2SO4, filtered and concentrated under reduced pressure to afford crude 2-amino-4-bromo-phenol as a yellow solid (3.9 g, 75%): 1H NMR (200 MHz, DMSO-d6): δ 9.27 (s, 1H), 6.70 (d, J=2.2 Hz, 1 H), 6.50 (m, 2 H), 4.79 (s, 2 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=20% ethyl acetate in hexanes; Rf=0.35.

Provenance & Evidence