Under nitrogen protection, 1,2-dibromobenzene (20.0 g, 84.78 mmol), 4-chlorophenylboronic acid (30.49 g, 194.99 mmol), tetrakis(triphenylphosphine)palladium (4.89 g, 4.24 mmol) and potassium carbonate (28.10 g, 203.33 mmol) were dissolved in a mixed solvent of toluene (150 mL), water (150 mL) and ethanol ( 150 mL) in a solvent mixture. The reaction mixture was stirred at 100 °C for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane, the organic phases were combined and concentrated under reduced pressure. Purification by column chromatography afforded 19.5 g of the target product 4,4''-dichloro-1,1':2',1''-terphenyl.
