Hydrochloric Acid → 6-(Dibenzofuran-2-yl)naphthalene-2-ylboronic acid

Participants

Reaction Conditions

Reaction Steps

In argon atmosphere, a liquid mixture of 7.47 g (20.0 mmol) of 2-(6-bromonaphthalene-2-yl)dibenzofuran and 75 ml of dry THF was cooled to −60° C., and 15.5 ml (24.0 mmol) of a 1.55 M hexane solution of n-butyllithium was added dropwise under stirring. Further, the reaction mixture was stirred at −70° C. for 2 h. The reaction solution was cooled again to −70° C., and 11.29 g (60.0 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 reaction mixture was cooled on an ice bath, added with a 6 N hydrochloric acid, and stirred at room temperature for one hour. After adding dichloromethane, the reaction mixture was allowed to separate into liquid phases, and the organic phase was washed with water and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel chromatography to obtain 4.20 g (yield: 62%) of 6-(dibenzofuran-2-yl)naphthalene-2-ylboronic acid.

Provenance & Evidence