Thionyl Chloride → 2-(1-Chloroethyl)pyridine
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7](O)[CH3:8].S(Cl)([Cl:12])=O>ClCCl>[Cl:12][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
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.