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

HRID 895688
Notes
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Reaction equation

HRID 895688 reaction equation
[C:1]([C:3]1[C:4]([C:10]([F:13])([F:12])[F:11])=[N:5][N:6]([CH3:9])[C:7]=1[CH3:8])#[CH:2].C(P(C(C)(C)C)C1C=CC=CC=1)(C)(C)C.[F:29][C:30]([F:43])([F:42])[C:31]1[CH:32]=[C:33](Br)[CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1.C1(N(C)C)CCCCC1.Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I.CC(N(C)C)=O>[C:1]([C:3]1[CH:4]([C:10]([F:12])([F:13])[F:11])[N:5]([C:33]2[CH:34]=[C:35]([C:37]([F:40])([F:38])[F:39])[CH:36]=[C:31]([C:30]([F:29])([F:43])[F:42])[CH:32]=2)[N:6]([CH3:9])[C:7]=1[CH3:8])#[CH:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7415N,N-DimethylcyclohexylamineHCID 676021-Bromo-3,5-bis(trifluoromethyl)benzeneHCID 316378Di-tert-butylphenylphosphineHCID 104424634-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazole

Product 1

HCID 87971815
4-Ethinyl-1,5-dimethyl-3-(trifluoromethyl)-1h-pyrazolyl-3,5-bis(trifluoromethyl)benzene
Yield 85%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

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.

Workup

  1. customAfter the end of the reaction
  2. temperaturethe mixture is cooled
  3. extractionextracted with ether
  4. dry with materialThe combined ether phases which have been dried over MgSO4
  5. concentrationare concentrated
  6. customThe product is obtained as a solid in an 85% yield

Sources & evidence

ORD record
ord-6c2984325c8a48a6a964e12c61587623
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06916839B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes