179056-04-3

288-36-8

459-57-4

41498-10-6

179056-04-3

To a solution of 4-fluorobenzaldehyde (2 g, 16 mmol) in DMF (50 mL) was added 1H-1,2,3-triazole (1.32 g, 19.2 mmol) and potassium carbonate (3.3 g, 24 mmol) under the protection of argon and stirred at room temperature. The reaction mixture was then heated to 100 °C and stirred continuously for 5 hours. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was diluted with ice-cold water (35 mL) and extracted with ethyl acetate (2 x 40 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using 20% ethyl acetate/hexane as eluent to give compound 418 (800 mg, 29% yield); switching to 40% ethyl acetate/hexane elution to give compound 419 (1 g, 36% yield), both as yellow solids.