Thionyl Chloride → 3-(Chloromethyl)-2-methylpyridine

Participants

Reaction Conditions

Reaction Steps

In a 50 ml round bottomed flask, under argon at 0° C., thionyl chloride (12 mL, 164 mmol) was cautiously added to (2-methyl-3-pyridinyl)methanol (8 g, 65.0 mmol). Process was exothermic and white fumes were formed. At the end of the addition the obtained brown solution was heated at 85° C. for 40 minutes. The reaction mixture was evaporated to get the crude material as solid yellow slurry that was then taken up with NaHCO3 saturated solution (300 ml)/DCM (300 ml). The phases were separated and the aqueous one back extracted with DCM (2×200 ml). The combined organics were dried over Na2SO4 and evaporated to dryness to get 3-(chloromethyl)-2-methylpyridine (8.7 g) as a black/brown waxy solid that was used without further purification in the next step.

Provenance & Evidence