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

Participants

Reaction Steps

A solution of 2-bromo-5-methoxybenzoic acid (10.00 g, 43.3 mmol) in dry THF (40 ml) was treated with borane in THF (65 ml of 1.0M solution, 65 mmol) at room temperature under nitrogen. After stirring for 4 h, no starting material was detectable by tic. Excess borane was quenched by careful addition of water over 30 min, and the solvent was evaporated under reduced pressure. The residue was partitioned between ether and 5% Na2CO3. The ether layer was washed with 5% Na2CO3, water, and brine, and dried over MgSO4. Filtration and removal of solvent left a colorless oil which solidified (9.11 g, 97%); tlc (silica gel, CH2Cl2, Rf 0.25). This material was used without further purification.

Provenance & Evidence