Bromoacetonitrile → 2-(4-Fluoro-1H-pyrazol-1-yl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (306 mg, 12.78 mmol, 60% oil dispersion) was suspended in tetrahydrofuran and the suspension was cooled to 0° C. A solution of 4-fluoro-1H-pyrazole (1.0 g, 11.62 mmol) and 2-bromoacetonitrile (1.39 g, 11.62 mmol) in tetrahydrofuran at 0° C. was added dropwise over a period of 40 min. The reaction mixture was stirred at room temperature for 12 h, and then a saturated aqueous solution of ammonium chloride was added. The mixture was extracted with diethyl ether, and the organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 5-10% ethyl acetate in petroleum ether) to afford 2-(4-fluoro-1H-pyrazol-1-yl)acetonitrile (1 g).

Provenance & Evidence