A mixed solution of 208.8 g (737.4 mmol) of 1-(4-bromophenyl)naphthalene with 2.1 L of anhydrous tetrahydrofuran (THF) was cooled to -60 °C under argon protection. Subsequently, 567 mL (884.9 mmol) of 1.56 M n-butyllithium hexane solution was added slowly dropwise under stirring conditions. After the dropwise addition was completed, the reaction mixture was continued to be stirred at -60 °C for 2 hours. Maintaining the temperature at -60 °C, 416 g (2.21 mol) of triisopropyl borate was added dropwise to the reaction system. After completion of the dropwise addition, the reaction mixture was gradually warmed to room temperature and stirred for 17 hours. At the end of the reaction, an aqueous hydrochloric acid solution was added to the mixture and stirred for 1 hour at room temperature. The reaction mixture was extracted with toluene, and the aqueous phase was separated and discarded. The organic phase was dried with magnesium sulfate and the solvent was removed by distillation under reduced pressure. The resulting solid was purified by recrystallization from toluene to give 126 g of 4-(1-naphthyl)phenylboronic acid in 67% yield.
