Bromoacetonitrile → HCID 89854165, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (631 mg, 16 mmol) was added to a solution of 4-(methylthio)-1H-pyrazole (1500 mg, 13.14 mmol) in anhydrous tetrahydrofuran (30 mL) under nitrogen at 0° C. The reaction mixture was stirred at 0° C. until gas evolution was no longer observed. Bromoacetonitrile (1.005 mL, 14.43 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 18 h. The mixture was poured into a solution of aqueous ammonium chloride (30 mL) and was extracted with ethyl acetate (60 mL×3). The combined organics were dried over sodium sulfate. The residue was filtered through a plug of silica gel which was eluted with ethyl acetate and the filtrate was concentrated under reduced pressure. The crude material was purified via flash chromatography (0-50% ethyl acetate in heptanes) to afford 2-(4-(methylthio)-1H-pyrazol-1-yl)acetonitrile (1460 mg, 72.54%). MS (ES+) (M+H) 154.1; LCMS retention time 0.40 min (Method N).

Provenance & Evidence