Thionyl Chloride → 2-Chloro-3-chloromethyl-pyridine

To a solution of the compound (18.5 g) obtained in step 1 in a mixture of chloroform (95 mL) and DMF (0.63 mL) was added thionyl chloride (14.0 mL) at 0° C., and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated under reduced pressure, and the residue was poured into a mixture of water and ethyl acetate. The solution was neutralized with sodium hydrogen carbonate, and the resultant product was extracted with ethyl acetate. The organic layer was washed with brine, and concentrated to give 2-chloro-3-(chloromethyl)pyridine (20.5 g, 89%) as a white powder.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionthe residue was poured into a mixture of water and ethyl acetate
3. extractionthe resultant product was extracted with ethyl acetate
4. washThe organic layer was washed with brine
5. concentrationconcentrated

ORD record

ord-3aa683d968f74603bc1abfee4f64c60f

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158617B2