Azobisisobutyronitrile → 2-(Bromomethyl)-3-methoxypyrazine

Participants

Reaction Steps

2-methoxy-3-methylpyrazine (0.943 mL, 8.06 mmol), N-bromosuccinimide (1.505 g, 8.46 mmol) and 2,2′-azobis(2-methylpropionitrile) (0.132 g, 0.806 mmol) were heated at reflux in CCl4 (65.5 mL) (oil bath=100° C.) for 2.5 h. LCMS indicated formation of the product. The crude mixture was cooled, filtered and purified by flash chromatography (SiO2, Biotage 40M cartridge). The column was eluted with a CH2Cl2/hexanes mixture (0% to 100%). Related fractions were pooled and co-evaporated with toluene to afford a toluene solution (30 mL) of the product. To be used as it was for next step.

Provenance & Evidence