Tricyclohexylphosphine → Methyl 2-cyclopropyl-4-(trifluoromethyl)benzoate

HRID 1690273

반응식

HRID 1690273 반응식
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1Br.[CH:16]1(B(O)O)[CH2:18][CH2:17]1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[CH:16]1[CH2:18][CH2:17]1

참가 물질

8

반응물 4

HCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 46311084Methyl 2-bromo-4-(trifluoromethyl)benzoate

생성물 1

HCID 59438487Methyl 2-cyclopropyl-4-(trifluoromethyl)benzoate수율 71%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a solution of 400 mg (1.413 mmol) 2-bromo-4-trifluoromethyl-benzoic acid methyl ester, 146 mg (1.696 mmol) cyclopropyl boronic acid, 1.21 g (4.946 mmol) tri-potassium phosphate monohydrate, 40.9 mg (0.141 mmol) tricyclohexyl phosphine in 6 ml toluene and 0.3 ml water under nitrogen at room temperature, was added 15.9 mg (0.0707 mmol) palladium acetate. The mixture was stirred in a 100° C. oil bath for 4 hours and overnight at room temperature under nitrogen. The mixture was cooled to room temperature. Water was added and the mixture extracted with ethyl acetate. The organic layer was washed once with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 10%) to provide 0.24 g (71%) of the title compound as a yellow oil.

후처리

  1. customovernight
  2. customat room temperature
  3. temperatureThe mixture was cooled to room temperature
  4. extractionthe mixture extracted with ethyl acetate
  5. washThe organic layer was washed once with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude compound was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 10%)

출처 및 근거

ORD 기록
ord-0a806f7f6e524a92b72dc9a442dae54d
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153653B2

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