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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1413204Generated: November 3, 2026

Sodium Carbonate → 2-Chloro-5-(trifluoromethyl)pyridine

https://huagongshe.com/reaction/1413204

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantThionyl ChlorideHCID 24386—
ReactantHCID 178516044HCID 178516044—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product2-Chloro-5-(trifluoromethyl)pyridineHCID 92342—
ProductHCID 178516044HCID 178516044—

Reaction Conditions

Temperature60 °C

Reaction Steps

30 g of thionyl chloride was added to 12 g of 2-hydroxy-5-trifluoromethylpyridine dissolved in 20 g of dimethylformamide. The 2-hydroxy-5-trifluoromethylpyridine was prepared as disclosed in Examples 4 and 5 of applicant's copending application earlier referred to and incorporated herein by reference. The solution was then heated to 60° C. for 24 hours, cooled to 20° C. and diluted with 200 cc of water and the pH adjusted to 5.5 with sodium carbonate. The acid solution was extracted three times with 100 cc of chloroform each time and the extracts washed three times with 20 cc of water each time. The chloroform solution was evaporated at reduced pressure to give 2-chloro-5-trifluoromethylpyridine.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04249009
Source datasetuspto-grants-1981_02
ORD IDord-646d01ba02c74014aa5e40930bcbad8b
Source noteuspto-grants-1981_02