Thionyl Chloride → 2-(Chloromethyl)-6-methylpyridine

A solution of (6-methyl-pyridin-2-yl)-methanol (1.44 g, 11.7 mmol), thionyl chloride (1.45 mL, 19.9 mmol) and methylene chloride (20 mL) was stirred under reflux for 40 minutes. The reaction solution was cooled to room temperature and then concentrated under a reduced pressure. The residue was partitioned into sodium bicarbonate solution and diethyl ether. The organic layer was concentrated under a reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate) to obtain the title compound (1.42 g, 85.8%).

1. temperatureunder reflux for 40 minutes
2. concentrationconcentrated under a reduced pressure
3. customThe residue was partitioned into sodium bicarbonate solution and diethyl ether
4. concentrationThe organic layer was concentrated under a reduced pressure
5. customthe residue was purified by silica gel chromatography (ethyl acetate)

ORD record

ord-78e6bd01107849bd8231580d44d84968

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2