Thionyl Chloride → 5-(Chloromethyl)-2-methylpyridine

Participants

Reaction Conditions

Reaction Steps

In a 250 ml round-bottomed flask at room temperature under nitrogen, (6-methyl-3-pyridinyl)methanol (4.32 g, 35.1 mmol, D8) was dissolved in dry dichloromethane (45 ml) to give a yellow solution, which was cooled down to 0° C. Thionyl chloride (3 ml, 41.1 mmol) was then added. The resulting pale-orange mixture was stirred at 0° C. for 15 minutes and at room temperature for 2 hours. The mixture was concentrated in vacuum and the brown residue was partitioned between DCM (150 ml) and saturated NaHCO3 (100 ml). Phases were separated and the organic was washed with saturated NaHCO3 (2×100 ml), dried over Na2SO4, filtered and concentrated to give the desired compound as brown oil (4.26 g), that was used without further purification in the next step.

Provenance & Evidence