Hydrochloric Acid → (4-(Phenanthren-9-yl)phenyl)boronic acid

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence