反应详情

温度

-70 °C

In argon atmosphere, a liquid mixture of 12.27 (32.01 mmol) of 7-bromo-2-(9-phenanthrenyl)naphthalene and 130 ml of dry THF was cooled to −70° C., and 24.8 ml (38.4 mmol) of a 1.56 M hexane solution of n-butyllithium was added dropwise under stirring. Further, the reaction mixture was stirred at −70° C. for 4 h. The reaction mixture was added dropwise with 18.06 g (96.04 mmol) of triisopropyl borate while maintaining the temperature at −60° C. or lower and then stirred for one hour. The reaction mixture was heated, stirred at room temperature for 3 h, and then allowed to stand overnight. The reaction mixture was added with 100 ml of a 6 N hydrochloric acid while maintaining the temperature at 20° C. or lower by cooling on an ice bath. The reaction mixture was stirred at room temperature for 30 min, added with dichloromethane, and then allowed to separate into liquid phases. The organic phase was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation to obtain 9.50 g (yield: 85%) of 2-(9-phenanthrenyl)naphthalene-7-boronic acid.

1. stirringFurther, the reaction mixture was stirred at −70° C. for 4 h
2. temperaturewhile maintaining the temperature at −60° C.
3. stirringlower and then stirred for one hour
4. temperatureThe reaction mixture was heated
5. stirringstirred at room temperature for 3 h
6. temperaturewhile maintaining the temperature at 20° C.
7. temperaturelower by cooling on an ice bath
8. stirringThe reaction mixture was stirred at room temperature for 30 min
9. customto separate into liquid phases
10. washThe organic phase was washed with water
11. dry with materialdried over anhydrous sodium sulfate
12. customThe solvent was removed by distillation