3.1. General experimental procedure for the synthesis of 4-(1H-[1,2,4]-triazol-1-yl)benzaldehyde (3)
To a solution of 4-fluorobenzaldehyde (1) (5.0 g, 40.32 mmol) and 1H-[1,2,4]-triazole (2) (3.3 g, 47.82 mmol) in DMF (50 mL) was added powdered K2CO3 (6.67 g, 48.38 mmol). The mixture was stirred at 120 °C for 12 h. Reaction mixture was warmed up at room temperature and quenched with water. It was extracted with ethylacetate (2 × 150 mL). The combined organic fractions were washed with water (100 mL) followed to brine solution (100 mL) and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure and purification was done by flash chromatography (hexane:ethylacetate, 3:1 elution) to give 4-(1H-[1,2,4]-triazol-1-yl)benzaldehyde as a off-white solid (3) (5.0 g, 72% yield). 1H NMR (CDCl3) δ (ppm): 8.01–8.10 (4H, m), 8.15 (1H, s, triazole-H), 9.43 (1H, s, ArH), 10.10 (1H, s, CHO). m/z 173 (M+).
发表于 2013-4-29 13:53:13
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发表于 2013-4-29 13:53:14
