Hydrochloric Acid → (6-Phenylnaphthalen-2-yl)boronic acid

Participants

Reaction Conditions

Reaction Steps

Under an argon gas atmosphere, a mixture of 100.0 g (353.1 mmol) of 2-bromo-6-phenylnaphthalene, 1.2 L of dehydrated THF and 1.2 L of dehydrated diethyl ether was cooled down to minus 20 degree C. Then, 280 ml (437 mmol) of hexane solution of 1.56M n-butyllithium was dropped into the mixture while the mixture was being stirred. The reaction mixture was further stirred at minus 20 degrees for 1 hour. The reaction mixture was cooled down to minus 60 degrees C., and 199.3 g (1.06 mol) of triisopropylborate was dropped into the mixture. The reaction mixture was warmed up and then stirred at room temperature for 16 hours. The reaction mixture was added with aqueous solution of hydrochloric acid and stirred at room temperature for 1 hour. After the reaction, the reaction mixture was added with toluene, and aqueous phase thereof was eliminated. Then, organic phase thereof was washed with water and dried with magnesium sulfate, and the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid with hexane, 58.0 g of 6-phenylnaphthalene-2-boronic acid was obtained at an yield of 55%.

Provenance & Evidence