4-(4-Pyridinyl)benzaldehyde

1692-15-5

1122-91-4

99163-12-9

Pyridine-4-boronic acid (498.3 mg, 4.05 mmol) and p-bromobenzaldehyde (500 mg, 2.70 mmol) were added to bis(triphenylporphyrinophosphate) palladium dichloride Pd(PPh3)2Cl2 (94.65 mg, 0.14 mmol) as a catalyst and dissolved in 20 mL of a solvent mixture of tetrahydrofuran and toluene (Vtoluene: VTHF = 1:1) in it. The reaction mixture was heated to 90°C under nitrogen protection for reflux reaction and the reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction solution was concentrated to remove the organic solvent and subsequently extracted with ethyl acetate. The organic layer was washed sequentially with water three times, saturated sodium chloride solution once, and then dried with anhydrous sodium sulfate. The dried organic phase was evaporated under reduced pressure to remove the solvent to obtain the crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of petroleum ether and ethyl acetate (20:1) as eluent to finally obtain 4-(pyridin-4-yl)benzaldehyde (white solid, 288.7 mg, 68.4% yield).