Boron tribromide → HCID 135741338, compound

Participants

Reaction Steps

A 1.0 M dichloromethane solution of boron tribromide (12.26 mL, 12.26 mmol) was added to a solution of 2-chloro-4-(4-methoxyphenyl)nicotinonitrile (300 mg, 1.226 mmol) in dichloromethane (10 mL). The mixture was stirred at room temperature for 2 h, diluted with ethyl acetate (50 mL), and carefully quenched with saturated sodium bicarbonate (20 mL). The aqueous layer was separated and extracted with ethyl acetate (2×50 mL). The combined extracts were washed with water (30 mL), brine (30 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 10-50% ethyl acetate in hexanes, gave 2-chloro-4-(4-hydroxyphenyl)nicotinonitrile as a brown solid (50 mg, 18% yield). 1H NMR (500 MHz, CDCl3) δ ppm 8.55 (1H, δ, J=5.22 Hz), 7.49-7.62 (2H, m), 7.38 (1H, δ, J=5.22 Hz), 6.94-7.05 (2H, m); MS (ES+) m/z: 231 (M+H); LC retention time: 2.841 min (analytical HPLC Method A).

Provenance & Evidence