Acrylonitrile → 3,5-Bis(trifluoromethyl)cinnamonitrile

HRID 2212641

反応式

HRID 2212641 の反応式
[C:1](#[N:4])[CH:2]=[CH2:3].C1(P(C(C)(C)C)C(C)(C)C)C=CC=CC=1.[F:20][C:21]([F:34])([F:33])[C:22]1[CH:23]=[C:24](Cl)[CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1.C1(C(N)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CC(N(C)C)=O>[F:20][C:21]([F:33])([F:34])[C:22]1[CH:23]=[C:24]([CH:25]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:27]=1)[CH:3]=[CH:2][C:1]#[N:4]

参加物

8

反応物 4

HCID 7855AcrylonitrileHCID 316378Di-tert-butylphenylphosphineHCID 27694053,5-Bis(trifluoromethyl)chlorobenzeneHCID 10774245alpha-Cyclohexylcyclohexanemethanamine

生成物 1

HCID 27361763,5-Bis(trifluoromethyl)cinnamonitrile収率 69%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

実験手順

0.382 g (7.2 mmol) of acrylonitrile, 38.7 mg (120 μmol) of NBu4Br, 6.7 mg (30 μmol) of palladium acetate and 26.7 mg (120 μmol) of phenyldi(t-butyl)phosphine are weighed into a Schlenk vessel. 1.49 g (6 mmol) of 3,5-bis(trifluoromethyl)chlorobenzene and 1.53 ml (7.2 mmol) of dicyclohexylmethylamine and also 3.5 ml of dimethylacetamide are then added. The Schlenk vessel is placed in a heating bath at 130° C. and the contents are stirred. After 4 hours, the contents are poured into 30 ml of water and the product is extracted by shaking with t-butyl methyl ether. After drying the organic phase over MgSO4, the solvent is removed under reduced pressure and the product is isolated. Orange oil, yield: 69%.

後処理

  1. customThe Schlenk vessel is placed in a heating bath at 130° C.
  2. extractionthe product is extracted
  3. stirringby shaking with t-butyl methyl ether
  4. dry with materialAfter drying the organic phase over MgSO4
  5. customthe solvent is removed under reduced pressure
  6. customthe product is isolated

出典と根拠

ORDレコード
ord-fb848583d510498d9da13547449a7f6e
出典データセット
uspto-grants-2006_09
特許番号
US07102046B2

関連ノート

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