Thionyl Chloride → 2-(1-Chloroethyl)pyridine

Temperature

20 °C

To an ice-cooled solution of 1-(pyridin-2-yl)ethanol (4.5 g, 36 mmol) in dry dichloromethane (100 mL) was slowly added thionyl dichloride (20 mL). The mixture was then warmed to 20° C. After 2 h, the reaction was concentrated in vacuo, and the resulting residue was diluted with water (40 mL) and dichloromethane (60 mL). The solution was neutralized with saturated aqueous sodium carbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution (3×30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford crude 2-(1-chloroethyl)pyridine (5.0 g, 97% yield). The product was used without further purification.

1. concentrationthe reaction was concentrated in vacuo
2. additionthe resulting residue was diluted with water (40 mL) and dichloromethane (60 mL)
3. washThe organic layer was washed with saturated aqueous sodium chloride solution (3×30 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-87c1c71f9ea14145b19d528c91d25512

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365583B2