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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 536485Generated: October 30, 2026

Thionyl Chloride → 4-(Chloromethyl)-3-fluoropyridine hydrochloride

https://huagongshe.com/reaction/536485

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
Reactant(3-Fluoropyridin-4-yl)methanolHCID 49760376—
SolventAcetonitrileHCID 6342—
Product4-(Chloromethyl)-3-fluoropyridine hydrochlorideHCID 71306203—

Reaction Conditions

Temperature50 °C

Reaction Steps

6.710 g (52.785 mmol) of (3-fluoropyridin-4-yl)methanol was put in 29 ml acetonitrile and heated to 50° C. Then a solution of 7.701 ml thionyl chloride in 14.5 ml acetonitrile was added dropwise and the reaction mixture was stirred for 4 h at 50° C. Then the reaction mixture was concentrated by evaporation and was co-distilled three times with dichloromethane. After drying under high vacuum, 10.27 g of the title compound was obtained, which was used in the next step without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08859569B2
Source datasetuspto-grants-2014_10
ORD IDord-53cd80e5e96045c68d55a431d243c5a9
Source noteuspto-grants-2014_10