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, 1.2L of dehydrated THF and 1.2L of dehydrated diethylether was cooled down to −20 degrees C., and added with 280 ml (437 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for one hour at −20 degree C. The reaction mixture was further cooled down to −60 degrees C., and added with 199.3 g (1.06 mol) of triisopropyl borate in drops. The reaction mixture was subsequently warmed up to room temperature, and stirred for 16 hours at room temperature. The reaction mixture was further added with solution of hydrochloric acid to be stirred for one hour at room temperature. After the reaction, the reaction mixture was further added with toluene, so that aqueous phase thereof was eliminated. After organic phase thereof was cleansed with water and dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid by hexane, 58.0 g of 6-phenylnaphthalene-2-boronic acid was obtained at an yield of 55%.

Provenance & Evidence