Under argon protection, 1-naphthaleneboronic acid (200.0 g, 1.163 mol), 4-bromoiodobenzene (329.0 g, 1.163 mol), tetrakis(triphenylphosphine)palladium(0) (26.9 g, 23.3 mmol), toluene (3.7 L), and 2M aqueous sodium carbonate (1.74 L) were added to the reaction vessel. The reaction mixture was stirred at 90 °C for 24 hours. After completion of the reaction, the mixture was filtered to remove the aqueous phase. The organic phase was washed with water and subsequently dried with magnesium sulfate. The toluene solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography to afford 1-(4-bromophenyl)naphthalene (268 g, 81% yield).
