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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 33542Generated: October 29, 2026

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

https://huagongshe.com/reaction/33542

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantThionyl ChlorideHCID 24386—
Reactant(5-(3-Chlorophenyl)pyridin-3-yl)methanolHCID 24729846—
SolventDichloromethaneHCID 6344—
Product3-(Chloromethyl)-5-(3-chlorophenyl)pyridineHCID 69106407—

Reaction Conditions

Temperature0 °C

Reaction Steps

271 mg (0.165 ml, 2.28 mmol) thionyl chloride were added drop by drop at 0° C. to a solution of 0.2 ml N,N-dimethylformamide (DMF) and 250 mg (1.14 mmol) [5-(3-Chloro-phenyl)-pyridin-3-yl]-methanol in 20 ml dichloromethane and stirred for 3 h at 0° C. The mixture was poured on ice/sodium bicarbonate solution and the organic phase separated. The water phase was extracted with dichloromethane. The combined organic phases were washed with water, dried (sodium sulphate), evaporated and the obtained material (248 mg, 84%) used without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07429605B2
Source datasetuspto-grants-2008_09
ORD IDord-c4d58a1f9f3141559d0f09867fd52fcd
Source noteuspto-grants-2008_09