Hydrochloric Acid → 6-(9,9-dimethyl-9H-fluorene-2-yl)naphthalene-2-ylboronic acid

Participants

Reaction Conditions

Reaction Steps

In argon atmosphere, a liquid mixture of 12.00 g (30.1 mmol) of 2-(6-bromonaphthalene-2-yl)-9,9-dimethyl-9H-fluorene and 120 ml of dry THF was cooled to −70° C., and 23.3 ml (36.0 mmol) of a 1.55 M hexane solution of n-butyllithium was added dropwise while stirring. Then, the reaction mixture was stirred at −70° C. for 2 h. The reaction solution was cooled again to −70° C., and 17.0 g (90.2 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. The reaction mixture was added with dichloromethane and allowed to stand for separation of liquid phases. The organic phase was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography to obtain 6.25 g (yield: 57%) of 6-(9,9-dimethyl-9H-fluorene-2-yl)naphthalene-2-ylboronic acid.

Provenance & Evidence