Tetrahydrofuran → (4-Bromo-3,5-dimethoxyphenyl)methanol

Participants

Reaction Steps

To a mixture of 4-bromo-3,5-dimethoxybenzoic acid (50.0 g, 192 mmol) and THF (1 L) was added borane methyl sulfide (27.1 mL, 286 mmol) while cooling on ice, and the mixture was heated to reflux for one hour. Water was gradually added to the mixture while cooling on ice, and the solvent in the mixture was then distilled off under reduced pressure. To the residue, water and ethyl acetate were added. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (47.3 g, 191 mmol).

Provenance & Evidence