Carbon tetrabromide → 5-(Bromomethyl)-2,3-dichloropyridine

Participants

Reaction Steps

2,3-Dichloro-5-(hydroxymethyl)pyridine (275 mg) was dissolved in dichloromethane (10 ml) and stirred in the presence of triphenylphosphine (444 mg) and tetrabromometliane (641 mg) overnight. The solution was concentrated in vacuo and the residue purified by column chromatography using isohexane: 2.5% ethyl acetate as eluent to yield the product as a white solid (270 mg, 73%). NMR: δ 4.75 (s, 2H), 8.25 (m, 1H), 8.5 (m, 1H); m/z 242 (M+H+).

Provenance & Evidence