Hydrochloric Acid → (3-(Phenanthren-9-yl)phenyl)boronic acid

Temperatur

-60 °C

In argon atmosphere, a liquid mixture of 15.45 g (46.4 mmol) of 9-(3-bromophenyl)phenanthrene and 150 ml of dry THF was cooled to −60° C., and 35.9 ml (55.6 mmol) of a 1.55 M hexane solution of n-butyllithium was added dropwise under stirring. Then, the reaction mixture was stirred at −60° C. for 2 h. The reaction solution was cooled again to −60° C., and 26.2 g (139 mol) of triisopropyl borate was added dropwise. The reaction mixture was heated up to room temperature, stirred for one hour, and left standing overnight. The solvent was removed by distillation under reduced pressure to concentrate the reaction mixture. The concentrated reaction mixture was cooled to 0° C., added with hydrochloric acid, and stirred at room temperature for one hour. After the reaction, dichloromethane was added to the reaction mixture, and the aqueous phase was removed. The organic phase was dried over sodium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel chromatography to obtain 13.4 g (yield: 67%) of 3-(9-phenanthrenyl)phenylboronic acid.

1. stirringThen, 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 one hour
5. waitleft
6. customThe solvent was removed by distillation under reduced pressure
7. concentrationto concentrate the reaction mixture
8. customThe concentrated reaction mixture
9. temperaturewas cooled to 0° C.
10. stirringstirred at room temperature for one hour
11. additionwas added to the reaction mixture
12. customthe aqueous phase was removed
13. dry with materialThe organic phase was dried over sodium sulfate
14. customthe solvent was removed by distillation under reduced pressure
15. customThe residue was purified by silica gel chromatography

ORD-Eintrag

ord-2f85134bd655419fb1f425ddde0dbf67

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08940412B2