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

Temperature

85 °C

In a 50 ml round bottomed flask, under argon at 0° C., thionyl chloride (12 mL, 164 mmol) was cautiously added to (2-methyl-3-pyridinyl)methanol (8 g, 65.0 mmol). Process was exothermic and white fumes were formed. At the end of the addition the obtained brown solution was heated at 85° C. for 40 minutes. The reaction mixture was evaporated to get the crude material as solid yellow slurry that was then taken up with NaHCO3 saturated solution (300 ml)/DCM (300 ml). The phases were separated and the aqueous one back extracted with DCM (2×200 ml). The combined organics were dried over Na2SO4 and evaporated to dryness to get 3-(chloromethyl)-2-methylpyridine (8.7 g) as a black/brown waxy solid that was used without further purification in the next step.

1. customwhite fumes were formed
2. additionAt the end of the addition the obtained brown solution
3. customThe reaction mixture was evaporated
4. customto get the crude material as solid yellow slurry that
5. customThe phases were separated
6. extractionthe aqueous one back extracted with DCM (2×200 ml)
7. dry with materialThe combined organics were dried over Na2SO4
8. customevaporated to dryness

ORD record

ord-64553d63c3364eafb817eec1e5f03634

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173820B2