反应详情

温度

-78 °C

To a solution of 1-bromo-4-(4-(trifluoromethoxy)phenoxy)benzene (5.07 g, 15.2 mmol) in THF (76 ml) at −78° C. was added n-butyllithium (7.6 ml, 2.5 M in hexanes, 19.0 mmol) dropwise. The reaction mixture was stirred 0.5 hours at −78° C., and triisopropylborate (7.0 ml, 30.4 mmol) was added. The reaction was stirred 4 hours at room temperature, quenched with 1 N HCl and stirred 0.5 hours at 0° C. The aqueous layer was extracted with ethyl acetate. The combined organic layers were extracted with brine and dried over magnesium sulfate. Purification by silica gel chromatography (0-10% methanol in dichloromethane) provided 4.38 g (4-(4-(trifluoromethoxy) phenoxy) phenyl) boronic acid (97% yield) as a light brown viscous oil. 1H NMR (400 MHz, CDCl3) δ 8.20 (d, J=8.9 Hz, 1H), 7.26 (d, J=8.9 Hz, 1H), 7.07-7.14 (m, 2H).

1. stirringThe reaction was stirred 4 hours at room temperature
2. customquenched with 1 N HCl
3. stirringstirred 0.5 hours at 0° C
4. extractionThe aqueous layer was extracted with ethyl acetate
5. extractionThe combined organic layers were extracted with brine
6. dry with materialdried over magnesium sulfate
7. customPurification by silica gel chromatography (0-10% methanol in dichloromethane)