Hydrochloric Acid → HCID 57539854, compound

Participants

Reaction Conditions

Reaction Steps

Under an argon gas atmosphere, a mixture of 15.3 g (42.6 mmol) of 2-(4′-bromobiphenyl-4-yl)naphthalene and 200 mL of dehydrated THF was cooled down to −60 degrees C., and added with 32.8 mL (51.1 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for one hour at −60 degree C. The reaction mixture was further cooled down to −60 degrees C., and added with 24.0 g (1.06 mol) of triisopropyl borate in drops. Then, the mixture was warmed up to room temperature to be stirred for 16 hours. 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, 9.50 g of 4′-(naphthalene-2-yl)biphenyl-4-yl boronic acid was obtained at an yield of 67%.

Provenance & Evidence