Hydrochloric Acid → 4-ethenyl-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole

HRID 895684

반응식

HRID 895684 반응식
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].[C:13](P(C(C)(C)C)C1C=CC=CC=1)(C)(C)[CH3:14].C1(C(N)C2CCCCC2)CCCCC1.C=C.Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(N(C)C)=O>[CH:13]([C:2]1[C:3]([C:9]([F:12])([F:11])[F:10])=[N:4][N:5]([CH3:8])[C:6]=1[CH3:7])=[CH2:14]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 6325EthyleneHCID 316378Di-tert-butylphenylphosphineHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 118590454-Bromo-1,5-Dimethyl-3-(Trifluoromethyl)-1H-Pyrazole

생성물 1

HCID 223809904-ethenyl-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole수율 83%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 31374Dimethylacetamide용매

반응 조건

온도
130 °C

실험 절차

10.0 g (41.2 mmol) of 4-bromo-1,5-dimethyl-3-(trifluoromethyl)-1H-pyrazole, 92.4 mg (0.41 mmol) of palladium acetate and 302 mg (0.82 mmol) of tetra-n-butylammonium bromide are weighed into the glass insert of an autoclave together with 366 mg (1.65 mmol) of di(tert-butyl)phenylphosphine, 8.84 g (45.3 mmol) of dicyclohexylmethylamine and dimethylacetamide (34.3 ml), and placed under a protective gas atmosphere. Subsequently, 30 bar of ethylene are injected at 20° C. and the reaction mixture is stirred at 130° C. for 30 h. After the end of the reaction, the mixture is cooled, poured onto cold dilute hydrochloric acid and extracted with CH2C12. The combined organic phases which have been dried over magnesium sulphate are concentrated. The product is obtained as a brown oil in an 83% yield.

후처리

  1. customare injected at 20° C.
  2. customAfter the end of the reaction
  3. temperaturethe mixture is cooled
  4. extractionextracted with CH2C12
  5. dry with materialThe combined organic phases which have been dried over magnesium sulphate
  6. concentrationare concentrated
  7. customThe product is obtained as a brown oil in an 83% yield

출처 및 근거

ORD 기록
ord-c8276a13236144cc8ad83cac4d23efab
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916839B2

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