To a stirred solution of 2-iodo-3-hydroxypyridine (5.0 g, 22.624 mmol) in benzene (50 ml) was added phenylboronic acid (3.03 g, 24.85 mmol) and 2M Na2CO3 solution (20 mL) sequentially at 25 °C. The reaction system was protected and degassed with argon for 15 min. Tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.3 g, 5 mol%) was then added and degassing continued for 10 minutes. The reaction mixture was heated to reflux for 4 hours. After completion of the reaction, it was cooled to room temperature, water was added and extracted with ethyl acetate (EtOAc). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by solvent milling with methyl tert-butyl ether (MTBE)/dichloromethane (DCM) mixture to give 3-hydroxy-2-phenylpyridine (3.2 g).LCMS detection showed a molecular ion peak of 172 (M + H).
