Boron tribromide → HCID 12465308, compound

Participants

Reaction Conditions

Reaction Steps

Boron tribromide (1M in dichloromethane, 6.2 mL, 6.2 mmol) was added to a solution of 4-methoxy-3-methylphenylacetonitrile (0.2 g, 1.24 mmol) in dichloromethane (10 mL), cooled to −78° C. The reaction mixture was stirred at this temperature for 1 hour and then at room temperature for 2 hours. The mixture was then re-cooled to −78° C., diluted with sodium hydrogen carbonate solution and allowed to warm to room temperature. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound as a white solid in 87% yield, 0.16 g. 1H NMR (400 MHz, CDCl3) δ:7.07 (1H, s), 7.00 (1H, d), 6.76 (1H, d), 3.65 (2H, s), 2.25 (3H, s) ppm; LRMS APCI m/z 146 [M−H]−.

Provenance & Evidence