1,2-Dibromoethane → 1-(1-methyl-1H-1,2,4-triazol-5-yl)cyclopropanecarbonitrile

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Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 1.06 g, 44.2 mmol) was washed twice with petroleum ether under nitrogen. Then dimethylsulfoxide (10 mL) was added at room temperature. A solution of 2-(1-methyl-1H-1,2,4-triazol-5-yl)acetonitrile (0.9 g, 7.36 mmol) and 1,2-dibromoethane (4.147 g, 22.1 mmol) in dimethylsulfoxide (20 mL) was added dropwise to the sodium hydride suspension over a period of 20 min. The reaction mixture was stirred at room temperature for 3 h. The mixture was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 5-15% ethyl acetate in petroleum ether) to afford 1-(1-methyl-1H-1,2,4-triazol-5-yl)cyclopropanecarbonitrile (0.7 g) as a colorless oil.

Provenance & Evidence