Carbon Tetrachloride → 2,3-Bis(chloromethyl)pyrazine

Participants

Reaction Steps

To a solution of 2,3-dimethylpyrazine (6.27 g, 57.4 mmol) in 100 mL of carbon tetrachloride was added N-chlorosuccinimide (16.7 g) followed by benzoyl peroxide (278 mg, 2 mol %) and the solution was heated to reflux for 16 h. The reaction was cooled, more benzoyl peroxide (278 mg, 2 mol %) was added and the reaction was refluxed for 5 h. The reaction was monitored by TLC until the disappearance of starting pyrazine. The reaction flask was cooled in an ice bath, the solution filtered, and the eluent was concentrated and chromatographed on SiO2 using 15% EtOAc in hexane. Obtained 1.14 g of the product (11% yield). MS found: (M+H)+=178.

Provenance & Evidence