Borane → (2-Bromo-5-methoxyphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

Dissolve 2-bromo-5-methoxy-benzoic acid (2.25 g, 9.7 mmol) in THF (10 mL) and cool to 0° C. Add 1M borane in THF (48 mL, 48 mmol) and warm to room temperature. Upon completion, slowly pour reaction onto ice and saturated aqueous sodium bicarbonate. Extract with ethyl acetate and wash organic layer with water and saturated aqueous sodium bicarbonate. Dry with sodium sulfate, filter and concentrate in vacuo to yield 2.1 g (100%) of the title compound. 1H NMR (CDCl3) δ7.42 (d, J=8.8 Hz, 1H), 7.06 (d, J=3.1 Hz, 1H), 6.72 (dd, J=8.8, 3.1 Hz, 1H), 4.71 (s, 2H), 3.81 (s, 3H).

Provenance & Evidence