Boron tribromide → HCID 135830957, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-chloro-2-(4-hydroxyphenyl)-6-methoxybenzoxazole (240 mg) in dichloromethane (5 mL) cooled at −78° C. was added boron tribromide (5 mL, 1M solution in dichloromethane, 5.7 eq.). The mixture was stirred at −78° C. for 10 min, warmed to room temperature and stirred for 3 h. The mixture was poured onto ice/water and extracted with ethyl acetate. The organic layer was washed with brine and dried over MgSO4. Chromatography on a silica gel column (eluant: acetone-dichloromethane, gradient from 0:100 to 5:95) and trituration of the resulting solid in dichloromethane afforded the title compound (53 mg) as a solid. NMR (DMSO-d6): 10.31 (s, 1H), 10.17 (s, 1H), 7.98 (d, 2H, J=8.4 Hz), 7.06 (s, 1H), 6.95 (d, 2H, J=8.4 Hz), 6.87 (s, 1H); MS: 262 (MH+); HPLC tR: 1.99 min.

Provenance & Evidence