HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 895688Generated: October 30, 2026
Hydrochloric Acid → 4-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazolyl-3,5-bis(trifluoromethyl)benzene
https://huagongshe.com/reaction/895688
Participants
| Role | Name | HCID | Charge |
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| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | N,N-Dimethylcyclohexylamine | HCID 7415 | — |
| Reactant | 1-Bromo-3,5-bis(trifluoromethyl)benzene | HCID 67602 | — |
| Reactant | Di-tert-butylphenylphosphine | HCID 316378 | — |
| Reactant | 4-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazole | HCID 10442463 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | 4-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazolyl-3,5-bis(trifluoromethyl)benzene | HCID 87971815 | 85% |
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(tert-butyl)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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06916839B2 |
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| Source dataset | uspto-grants-2005_07 |
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| ORD ID | ord-6c2984325c8a48a6a964e12c61587623 |
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| Source note | uspto-grants-2005_07 |
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