105365-50-2

23703-22-2

105365-50-2

A n-hexane solution of n-butyllithium (1.67 M, 131 mL, 218 mmol) was slowly added dropwise to a solution of anhydrous THF (300 mL) of 1-bromo-4-hexylbenzene (50.0 g, 207 mmol) under nitrogen protection, keeping the reaction temperature at -75 °C. After the dropwise addition was completed, stirring of the reaction mixture was continued for 2 hours. Subsequently, trimethoxyborane (64.6 g, 622 mmol) was slowly added dropwise to the reaction system, and after completion of the dropwise addition, stirring was continued for 2 hours. At the end of the reaction, 1N dilute hydrochloric acid (300 mL) was slowly added to the reaction system and stirred for 30 minutes. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the intermediate 4-N-hexylphenylboronic acid (42.5 g, 99% yield) as a colorless solid.