Carbon tetrabromide → 2-(Bromomethyl)-3-fluoropyridine

Participants

Reaction Steps

A solution of 285 mg (2.242 mmol) of (3-fluoropyridin-2-yl)methanol (CAS: 31181-79-0) in dry dichloromethane (9 ml) in an ice-water bath and under an argon atmosphere was admixed with 882 mg (3.36 mmol) of triphenylphosphine and 1.12 g (3.36 mmol) of tetrabromomethane. The reaction mixture was stirred at room temperature for 22 hours. The solvent was evaporated off and the residue was purified by flash chromatography using a prepacked silica gel cartridge (mobile phase: cyclohexane-ethyl acetate, gradient 15% to 30%), which gave 156 mg (11% yield, 98% pure) of the target compound.

Provenance & Evidence