Carbon tetrabromide → 3-(Bromomethyl)-2-methyl-6-(trifluoromethyl)pyridine 1-oxide

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3-(hydroxymethyl)-2-methyl-6-(trifluoromethyl)pyridine 1-oxide (207 mg, 1.0 mmol) and carbon tetrabromide (400 mg, 1.2 mmol) in CH2Cl2 (5 mL) at 0° C. was added Ph3P (393 mg, 1.5 mmol) in small portions over 5 min. The reaction mixture was then stirred at 0° C. for 30 min. Analysis by HPLC/MS indicated the reaction was complete. The reaction mixture was directly loaded onto a silica gel cartridge (40 g) and eluted with a gradient of EtOAc (0-100%) in hexanes to afford 202 mg (75%) of the title compound as a white solid. HPLC/MS: retention time=2.10 min, [M+H]+=269.9.

Provenance & Evidence