Methanol → 5-Amino-2-fluorophenol

Participants

Reaction Steps

To a mixture of 4-fluoro-3-methoxyaniline (2.0 g, 14.2 mmol) in CH2Cl2 (20 mL) at 0° C. was added 1.0 M solution of BBr3 in CH2Cl2 (40 mL). It was stirred overnight, at which time the temperature was raised to room temperature. To it was added MeOH and the solvents were removed under reduced pressure. To the residue was added water, basified with saturated NaHCO3, and extracted with EtOAc. Extracts were washed with brine, dried over MgSO4, and concentrated under reduced pressure to afford 5-amino-2-fluorophenol as solid (1.3 g, 73%). 1H NMR (300 MHz, DMSO-d6) δ 9.26 (s, 1H), 6.81 (dd, 1H), 6.34 (dd, 1H), 6.04 (dd, 1H), 4.63 (br, 2H).

Provenance & Evidence