5-Fluoro-2-nitrophenol → 2-Amino-5-fluorophenol

Participants

Reaction Steps

A suspension of 3-fluoro-6-nitrophenol (500 mg, 3.18 mmol) and zinc (2.10 g, 31.8 mmol) in acetic acid (7.3 mL) was stirred overnight at room temperature. The reaction mixture was filtered through celite and washed with DCM. After evaporation and distillation under vacuum (2.10−2 mbar) of the solvents, the residue was dissolved in DCM. The organic phase was washed with a saturated solution of NaHCO3 and brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (DCM/MeOH 99.5:0.5) to yield 177 mg (1.39 mmol, 44%) of 2-amino-5-fluorophenol as an orange solid.

Provenance & Evidence