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

Thionyl chloride (9.2 mL, 126 mmol) was added dropwise to a solution of (6-methoxy-pyridin-3-yl)-methanol (1.00 g, 7.2 mmol) in dichloromethane (38 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and dichloromethane (100 mL) was added. The solution was washed with saturated aqueous sodium hydrogen carbonate (this resulted in bubbling). The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×100 mL). The combined organic layers were washed with brine (150 mL), dried (sodium sulfate), filtered, and evaporated to give 5-chloromethyl-2-methoxy-pyridine (995 mg, 88%) as a clear oil.

1. customThe solvent was evaporated
2. additiondichloromethane (100 mL) was added
3. washThe solution was washed with saturated aqueous sodium hydrogen carbonate (
4. customthis resulted
5. customin bubbling)
6. customThe organic layer was separated
7. extractionthe aqueous layer was extracted with dichloromethane (2×100 mL)
8. washThe combined organic layers were washed with brine (150 mL)
9. dry with materialdried (sodium sulfate)
10. filtrationfiltered
11. customevaporated

ORD record

ord-2766b80c5634451c85a16c9089a92dda

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622492B2