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

HRID 895684

反応式

HRID 895684 の反応式
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]

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 167845palladium(II) acetate触媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c8276a13236144cc8ad83cac4d23efab
出典データセット
uspto-grants-2005_07
特許番号
US06916839B2

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