In a three-necked flask, p-bromoiodobenzene (28 g, 0.1 mol), pyridine-3-boronic acid (12.3 g, 0.1 mol), potassium carbonate (27.2 g, 200 mmol), tetrakis(triphenylphosphine)palladium (0.8 g), tetrahydrofuran (200 ml) and water (50 ml) were added. The reaction mixture was heated to reflux for 5 hours under nitrogen protection. After completion of the reaction, it was cooled to room temperature and filtered to remove insoluble material. The filtrate was purified by column chromatography to give 13 g of 3-(4-bromophenyl)pyridine in 56% yield.
