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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 971085Generated: October 27, 2026

Vinyl Chloride → 4-(2-chloroethenyl)-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole

https://huagongshe.com/reaction/971085

Reaction equation

Participants

RoleNameHCIDCharge
ReactantVinyl ChlorideHCID 6338—
Reactantalpha-CyclohexylcyclohexanemethanamineHCID 10774245—
Reactant4-Bromo-1,5-Dimethyl-3-(Trifluoromethyl)-1H-PyrazoleHCID 11859045—
CatalystHydroquinoneHCID 785—
CatalystTetrabutylammonium BromideHCID 74236—
Catalystpalladium(II) acetateHCID 167845—
CatalystDi-tert-butylphenylphosphineHCID 316378—
SolventDimethylacetamideHCID 31374—
Product4-(2-chloroethenyl)-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazoleHCID 8515124083%

Reaction Conditions

Temperature140 °C

Reaction Steps

2.0 g of 4-bromo-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole together with 18.5 mg of palladium acetate, 73.2 mg of di(tert-butyl)phenylphosphine, 60.3 mg of tetrabutylammonium bromide, 10 mg of hydroquinone, 1.8 g of dicyclohexylmethylamine and 23 ml of dimethylacetamide are placed in a stainless steel autoclave. 2.6 g of vinyl chloride are condensed into this autoclave at low temperature and the autoclave is subsequently closed. It is subsequently heated at 140° C. for 20 hours. It is then cooled and depressurized and the reaction mixture is dewatered and worked up by extraction. 1.53 g (83% of theory) of 4-(2-chloroethenyl)-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole are isolated.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07312350B2
Source datasetuspto-grants-2007_12
ORD IDord-699bf78e54b74941b395188457daa115
Source noteuspto-grants-2007_12