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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence