Boron tribromide → 2-(3-Hydroxyphenyl)acetonitrile

Participants

Reaction Steps

To a solution of 2-(3-Methoxyphenyl)acetonitrile (3.6 g, 25.4 mmol) in dry methylene chloride (20 ml) was added BBr3 (55 ml, 1M in CH2Cl2, 55 mmol) at −78° C. under argon atmosphere. The reaction mixture was warmed to ambient temperature for 48 hours, quenched by crushed ice, and extracted with methylene chloride. The organic layer was dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (CH2Cl2:ethyl acetate 4:1) to give the title compound as oil.

Provenance & Evidence