4-(pyridin-2-yl)phenylboronic acid

63996-36-1

121-43-7

170230-27-0

5.0 g (21.36 mmol) of 2-(4-bromophenyl)pyridine (Compound 1) was dissolved in 30 mL of anhydrous tetrahydrofuran (THF) under nitrogen protection. The reaction system was cooled to -78 °C using an acetone/liquid nitrogen bath. Subsequently, 11.2 mL (2.5 M) of n-butyllithium (n-BuLi) solution was added slowly dropwise using a syringe. The temperature was maintained at -78 °C and the reaction was stirred for 1 hour. Under nitrogen atmosphere, 7.4 mL (64.08 mmol) of trimethyl borate (B(OMe)3) was added to the reaction mixture. The cooling bath was removed and the reaction mixture was allowed to gradually warm up to room temperature and stirring was continued for 16 hours. Upon completion of the reaction, the reaction was burst with water and the mixture was extracted with dichloromethane (CH2Cl2). The organic phase was dried with anhydrous sodium sulfate, concentrated and precipitated through petroleum ether to give a white solid. The solid was collected by filtration and dried under vacuum to give 2.80 g (65.8% yield) of the target product 4-(2-pyridyl)phenylboronic acid, the structure of the product was confirmed by NMR characterization.