Boron tribromide → HCID 136350295, compound

Participants

Reaction Steps

To a solution of 5-(7-methoxy-4,5-dihydronaphtho[2,1-d]thiazol-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole (Preparation 56B, 0.448 g, 1.046 mmol) in dichloromethane (13.07 mL) was added 1M BBr3 (5.23 mL, 5.23 mmol) in dichloromethane dropwise, and the mixture was stirred at room temperature for 4.5 h. The reaction was slowly quenched with sat. NaHCO3. After stirring for 5 min, sat. NH4Cl was added. It was then partitioned between dichloromethane and water. The aqueous layer was extracted with dichloromethane. The combined organic layers were then washed with brine, dried over anhydrous MgSO4, concentrated and chromatographed to give the 2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]thiazol-7-ol (0.388 g, 0.936 mmol, 90% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.63-7.69 (2H, m), 7.46-7.58 (3H, m), 7.31 (1H, d, J=8.14 Hz), 6.80 (1H, d, J=2.42 Hz), 6.76 (1H, dd, J=8.25, 2.53 Hz), 3.15-3.23 (2H, m), 3.05-3.14 (2H, m).

Provenance & Evidence