反应详情

温度

-60 °C

In argon atmosphere, a liquid mixture of 21.3 (63.9 mmol) of 9-(4-bromophenyl)phenanthrene and 200 ml of dry THF was cooled to −60° C. under argon atmosphere, and 49.2 ml (76.7 mmol) of a 1.55 M hexane solution of n-butyllithium was added dropwise under stirring. Further, the reaction mixture was stirred at −60° C. for 2 h. The reaction solution was cooled again to −60° C., and 36.1 g (192 mol) of triisopropyl borate was added dropwise. The reaction mixture was heated up to room temperature and stirred for 17 h. The reaction mixture was cooled to 0° C., added with hydrochloric acid, and stirred at room temperature for one hour. After the reaction, toluene was added to the reaction mixture and the aqueous phase was removed. The organic phase was dried over magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue was recrystallized from toluene and then from hexane to obtain 13.8 g (yield: 72%) of 4-(9-phenanthrenyl)phenylboronic acid.

1. stirringFurther, the reaction mixture was stirred at −60° C. for 2 h
2. temperatureThe reaction solution was cooled again to −60° C.
3. temperatureThe reaction mixture was heated up to room temperature
4. stirringstirred for 17 h
5. temperatureThe reaction mixture was cooled to 0° C.
6. stirringstirred at room temperature for one hour
7. additionwas added to the reaction mixture
8. customthe aqueous phase was removed
9. dry with materialThe organic phase was dried over magnesium sulfate
10. customthe solvent was removed by distillation under reduced pressure
11. customThe residue was recrystallized from toluene