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

HRID 971085Notes

Reaction equation

Br[C:2]1[C:3]([C:9]([F:12])([F:11])[F:10])=[N:4][N:5]([CH3:8])[C:6]=1[CH3:7].C1(C(N)C2CCCCC2)CCCCC1.[CH:27]([Cl:29])=[CH2:28]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1)(C)(C)C.C1(C=CC(O)=CC=1)O.CC(N(C)C)=O>[Cl:29][CH:27]=[CH:28][C:2]1[C:3]([C:9]([F:12])([F:11])[F:10])=[N:4][N:5]([CH3:8])[C:6]=1[CH3:7]

Participants

Conditions

Temperature: 140 °C

Procedure

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.

Workup

customcondensed into this autoclave at low temperature
customthe autoclave is subsequently closed
temperatureIt is then cooled
extractionworked up by extraction

Sources & evidence

ORD record: ord-699bf78e54b74941b395188457daa115
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312350B2

Reaction notes

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