Boron tribromide → HCID 136350296, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7-methoxy-8-methyl-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 64B, 0.130 g, 0.305 mmol) in dichloromethane (5 mL) at 0° C. was added boron tribromide (1.52 mL, 1.52 mmol). The reaction mixture was stirred at 0° C. for 1 h and then allowed to warm to room temperature and stirred overnight. The reaction mixture was partitioned between dichloromethane (25 mL) and water (25 mL). The dichloromethane extract was washed with a saturated aqueous solution of sodium bicarbonate (2×25 mL), washed with brine, dried over sodium sulfate, and concentrated. This crude product was filtered through a short silica gel pad, and the filtrate was concentrated to give 8-methyl-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-ol (0.121 g, 0.293 mmol, 96%) as a tan solid. The product had an HPLC ret. time=4.08 min (condition B). LC/MS M+1=413.30.

Provenance & Evidence