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

HRID 1293154
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HRID 1293154 반응식
[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]
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참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 167845palladium(II) acetate촉매HCID 31374Dimethylacetamide용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2135ce7514b2449581e5a475f9133f14
출처 데이터셋
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07238722B2

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