4-Ethoxy-2-fluoro-1-(phenylmethoxy)benzene → 4-Ethoxy-2-fluorophenol

Participants

Reaction Steps

10% Palladium-on-carbon (26 mg, 0.11 mmol) was added to a solution of 1-benzyloxy-4-ethoxy-2-fluoro-benzene (260 mg, 1.06 mmol) in ethyl acetate (20 mL). The reaction mixture was shaken under hydrogen (30 psi) overnight. The reaction mixture was filtered through celite and a pad of silica gel, which was washed with 40% ethyl acetate/hexane. The solvent was removed to give 4-ethoxy-2-fluoro-phenol (155 mg, 94%) as a white solid which was used directly in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ 1.25 (t, 3H, J=6.9 Hz), 3.89 (q, 2H, J=6.9 Hz), 6.52-6.56 (m, 1H), 6.71-6.85 (m, 2H), 9.21 (s, 1H).

Provenance & Evidence