Synthesis
GENERAL METHOD: A mixture of 4-fluorobenzaldehyde (10 mmol) and 1,2,4-triazole (10 mmol) was dissolved in anhydrous N,N-dimethylformamide (DMF, 20 mL). Potassium carbonate (K2CO3, 12 mmol) was added to the above stirred solution in portions over 15 minutes. The reaction mixture was stirred at 110°C for 10-12 hours. After completion of the reaction, the heating was stopped and the potassium carbonate was removed by filtration. The filtrate was extracted with ethyl acetate (3 x 15 mL). The organic layers were combined, washed with water (3 x 15 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (60-120 mesh) with the eluent of methanol:chloroform (1:99, v/v) to obtain the target compound 4-(1-1,2,4-triazolyl)benzaldehyde.
References
[1] European Journal of Medicinal Chemistry, 2009, vol. 44, # 7, p. 2930 - 2935
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 4302 - 4310
[3] Patent: US2012/329649, 2012, A1. Location in patent: Page/Page column 72
[4] Patent: US2014/171314, 2014, A1. Location in patent: Page/Page column
[5] Patent: WO2014/100163, 2014, A1. Location in patent: Page/Page column 131
