Benzoyl Peroxide → Methyl 6-(bromomethyl)pyridine-2-carboxylate

Participants

Reaction Steps

A mixture of methyl 6-methylpicolinate (1.81 g; 11.97 mmol) and carbon tetrachloride (60 mL) was treated with N-bromosuccinimide (2.37 g, 13.17 mmol) and benzoyl peroxide (0.299 g; 1.20 mmol) and heated at refluxing temperature for 21 hours. The resulting brown suspension was concentrated under reduced pressure and the residue purified by flash chromatography on silica gel (eluent 0 to 6% ethyl acetate in dichloromethane) to give 0.773 g (28%) of methyl 6-(bromomethyl)picolinate as a white solid.

Provenance & Evidence