Methyl Acrylate → Methyl 3,5-bis(trifluoromethyl)cinnamate

HRID 2212638

반응식

HRID 2212638 반응식
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].C1(P(C(C)(C)C)C(C)(C)C)C=CC=CC=1.[F:22][C:23]([F:36])([F:35])[C:24]1[CH:25]=[C:26](Cl)[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1.C1(C(N)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CC(N(C)C)=O>[F:22][C:23]([F:35])([F:36])[C:24]1[CH:25]=[C:26]([CH:27]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:29]=1)[CH:3]=[CH:2][C:1]([O:5][CH3:6])=[O:4]

참가 물질

8

반응물 4

HCID 7294Methyl AcrylateHCID 316378Di-tert-butylphenylphosphineHCID 27694053,5-Bis(trifluoromethyl)chlorobenzeneHCID 10774245alpha-Cyclohexylcyclohexanemethanamine

생성물 1

HCID 73856916Methyl 3,5-bis(trifluoromethyl)cinnamate

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 31374Dimethylacetamide용매

실험 절차

0.619 g (7.2 mmol) of methyl acrylate, 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. Yellowish, crystalline solid, yield: 1.34 g (97% of theory).

후처리

  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

출처 및 근거

ORD 기록
ord-e6aa1f3079e94bf5860ae4387b00b652
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07102046B2

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