Azobisisobutyronitrile → 5-(Bromomethyl)thiophene-2-carbonitrile

Participants

Reaction Steps

5-Methylthiophene-2-carbonitrile (500 mg, 4.06 mmol) in carbon tetrachloride (10 mL) was stirred with N-bromosuccinimide (867 mg, 4.87 mmol) and 2,2′-azobis(isobutyronitrile) (133 mg, 0.810 mmol) at 60° C. for 4.5 hours and allowed to cool to room temperature. After addition of saturated aqueous sodium thiosulfate, the reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1␣1/1 (v/v)) to give the title compound as a yellow oil (186 mg, yield 23%).

Provenance & Evidence