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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 33534Generated: October 29, 2026

Dimethylformamide → 3-(Chloromethyl)-5-(4-chlorophenyl)pyridine

https://huagongshe.com/reaction/33534

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantThionyl ChlorideHCID 24386—
Reactant(5-(4-Chlorophenyl)pyridin-3-yl)methanolHCID 24729853—
SolventDichloromethaneHCID 6344—
Product3-(Chloromethyl)-5-(4-chlorophenyl)pyridineHCID 69106423—

Reaction Conditions

Temperature0 °C

Reaction Steps

543 mg (0.333 ml, 4.56 mmol) thionyl chloride were added drop by drop at 0° C. to a solution of 0.2 ml N,N-dimethylformamide (DMF) and 500 mg (2.28 mmol) [5-(4-Chloro-phenyl)-pyridin-3-yl]-methanol in 30 ml dichloromethane and stirred for 2 h at 0° C. The mixture was poured on ice/sodium bicarbonate solution and the organic phase separated. The water phase is extracted with dichloromethane. The combined organic phases were washed with water, dried (sodium sulphate), evaporated and the obtained material (444 mg, 75%) used without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07429605B2
Source datasetuspto-grants-2008_09
ORD IDord-762e26e932fc4ce8b68c83898c1bd9b2
Source noteuspto-grants-2008_09