Thionyl Chloride → 3-(Chloromethyl)-2-methoxypyridine

Thionyl chloride (9.5 mL, 130 mmol) was added portionwise to a solution of (2-methoxy-pyridin-3-yl)-methanol (1.02 g, 7.3 mmol) in dichloromethane (36 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and dichloromethane (100 mL) was added. The solution was carefully treated with saturated aqueous sodium hydrogen carbonate and the mixture was stirred for 5-10 min. The organic layer was separated and the aqueous layer was extracted with dichloromethane (2×100 mL). The combined organic layers were washed with brine (100 mL), dried (sodium sulfate), filtered, and evaporated to give 3-chloromethyl-2-methoxy-pyridine (989 mg, 86%) as a light yellow oil.

1. customThe solvent was evaporated
2. additiondichloromethane (100 mL) was added
3. additionThe solution was carefully treated with saturated aqueous sodium hydrogen carbonate
4. stirringthe mixture was stirred for 5-10 min
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with dichloromethane (2×100 mL)
7. washThe combined organic layers were washed with brine (100 mL)
8. dry with materialdried (sodium sulfate)
9. filtrationfiltered
10. customevaporated

ORD record

ord-af9f06699f5145d6bcda6a6ba6dd1620

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622492B2