Hydrochloric Acid → HCID 86660652, compound

Participants

Reaction Conditions

Reaction Steps

In argon atmosphere, a liquid mixture of 16.00 (41.74 mmol) of 4-bromo-2-(9-phenanthrenyl)naphthalene and 160 ml of dry THF was cooled to −70° C., and 32.2 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 3 h. After adding 18.06 g (96.04 mmol) of triisopropyl borate while maintaining the temperature at −60° C. or lower, the mixture was stirred for one hour. The reaction mixture was heated, stirred at room temperature for 3 h, and left standing overnight. The reaction mixture was added with 50 ml of a concentrated hydrochloric acid while maintaining the temperature at 20° C. or lower by cooling on an ice bath and then stirred at room temperature for one hour. The reaction mixture was added with dichloromethane and allowed to separate into liquid phases. The organic phase was washed with water and dried over anhydrous sodium sulfate, and the solvent was removed by distillation. After recrystallizing from toluene, 5.40 g (yield: 37%) of 2-(9-phenanthrenyl)naphthalene-4-boronic acid was obtained.

Provenance & Evidence