Boron tribromide → 2-(3-Hydroxyphenyl)acetonitrile

Participants

Reaction Steps

Boron tribromide (68 ml, 1M in dichloromethane, 68 mmol) was added dropwise to an ice-cooled solution of (3-methoxyphenyl)acetonitrile (5.0 g, 34 mmol) in dichloromethane (50 ml), and once addition was complete, the reaction was allowed to warm to room temperature and stirred overnight. The reaction was poured into an ice/water solution, the mixture was basified using NaHCO3 and extracted with dichloromethane. The combined organic extracts were dried over MgSO4 and evaporated under reduced pressure to give the desired product as a brown oil, (4.13 g, 91%).

Provenance & Evidence