Thionyl Chloride → 3-(Chloromethyl)-2-cyclopropyl-6-(trifluoromethyl)pyridine

Participants

Reaction Steps

To a stirring solution of (2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)methanol (890 mg, 4.1 mmol) in dichloromethane (10 mL) at room temperature under argon was added thionyl chloride (730 mg, 6.1 mmol) followed by 3 drops of DMF. The reaction mixture was stirred at room temperature for 15 h. The reaction mixture was then concentrated under vacuum to obtain a light brown oil. This oil was diluted with EtOAc (20 mL) and washed with 10% aqueous Na2CO3 solution (20 mL). The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated to obtain 900 mg of the title compound as a light brown oil. HPLC/MS: retention time=3.66 min, [M+H]+=236.

Provenance & Evidence