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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1293154Generated: October 31, 2026

Hydrochloric Acid → 4-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazolyl-3,5-bis(trifluoromethyl)benzene

https://huagongshe.com/reaction/1293154

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantN,N-DimethylcyclohexylamineHCID 7415—
Reactant1-Bromo-3,5-bis(trifluoromethyl)benzeneHCID 67602—
ReactantDi-tert-butylphenylphosphineHCID 316378—
Reactant4-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazoleHCID 10442463—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
Catalystpalladium(II) acetateHCID 167845—
SolventDimethylacetamideHCID 31374—
Product4-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazolyl-3,5-bis(trifluoromethyl)benzeneHCID 8797181585%

Reaction Conditions

Temperature110 °C

Reaction Steps

183 mg (0.983 mmol) of 4-ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole, 2.3 mg (0.01 mmol) of palladium acetate and 3.9 mg (0.02 mmol) of copper(I) iodide are weighed into a round-bottom flask and placed under protective gas. Subsequently, 9.1 mg (0.04 mmol) of di(tertbutyl)phenylphosphine, 300 mg (1.03 mmol) of 3,5-bis(trifluoromethyl)bromobenzene, 137 mg (1.08 mmol) of cyclohexyldimethylamine and dimethylacetamide (5 ml) are added and the mixture is heated to 110° C. for 12 h. After the end of the reaction, the mixture is cooled, poured onto cold, dilute hydrochloric acid and extracted with ether. The combined ether phases which have been dried over MgSO4 are concentrated. The product is obtained as a solid in an 85% yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07238722B2
Source datasetuspto-grants-2007_07
ORD IDord-2135ce7514b2449581e5a475f9133f14
Source noteuspto-grants-2007_07