General procedure for the synthesis of 3-chloro-[1,1'-biphenyl]-4-carbaldehyde from 2-chloro-4-bromobenzaldehyde and phenylboronic acid: 4-bromo-2-chlorobenzaldehyde (2.19 g, 10.0 mmol) and phenylboronic acid (1.22 g, 10.0 mmol) were completely dissolved in tetrahydrofuran (50 mL), followed by the addition of 2M aqueous potassium carbonate (30 mL) and tetra( triphenylphosphine) palladium (Pd(PPh3)4, 231 mg, 0.2 mmol). The reaction mixture was stirred and refluxed for 5 hours. After completion of the reaction, it was cooled to room temperature and the resulting solid was collected by filtration. The solid was dissolved in chloroform, dried with anhydrous magnesium sulfate and subsequently concentrated under reduced pressure. Finally, the target product 3-chloro-[1,1'-biphenyl]-4-carbaldehyde (1.94 g, 90% yield) was purified by recrystallization from chloroform and hexane. Mass spectral analysis: [M]+ = 216.
