反应详情

To solution of 7-methoxy-2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]oxazole (Preparation 43B, 123 mg, 0.298 mmol) in dichloromethane (3 mL) was added 1 M boron tribromide (1.491 mL, 1.491 mmol) in dichloromethane dropwise, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched by the slow addition of saturated ammonium chloride, extracted with dichloromethane, washed with water and brine. The combined aq. layers were back extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate and evaporated to give a yellow crystalline solid (quantitative yield). 1H NMR (400 MHz, CDCl3 mixed with methanol-d4) δ ppm 7.66 (2H, d, J=6.82 Hz), 7.49-7.59 (4H, m), 7.46 (1H, d, J=8.58 Hz), 6.76-6.83 (2H, m), 3.14 (2H, t, J=7.70 Hz), 3.03 (2H, t, J=7.59 Hz).

1. customThe reaction mixture was quenched by the slow addition of saturated ammonium chloride
2. extractionextracted with dichloromethane
3. washwashed with water and brine
4. extractionThe combined aq. layers were back extracted with dichloromethane
5. dry with materialThe combined organic layers were dried over magnesium sulfate
6. customevaporated