2-Bromobenzyl cyanide → 2-(2-Cyclopropylphenyl)acetonitrile

HRID 254514

반응식

HRID 254514 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[CH:11]1(B(O)O)[CH2:13][CH2:12]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:11]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9]#[N:10])[CH2:13][CH2:12]1

참가 물질

8

반응물 4

HCID 296252-Bromobenzyl cyanideHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acid

생성물 1

HCID 589517752-(2-Cyclopropylphenyl)acetonitrile수율 63.6%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

To a solution of 0.784 g (4 mmol) 2-bromophenyl-acetonitrile in 16 ml toluene were added 0.8 ml water, 0.412 g (4.8 mmol) cyclopropylboronic acid, 2.97 g (14 mmol) tribasic potassium phosphate, 0.1 12 g (0.4 mmol) tricyclohexylphosphine and 0.045 g (0.2 mmol) palladium(II) acetate. The reaction mixture was stirred at 100° C. for 2 days. The solvent was evaporated and the residue taken up in water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified using column chromatography (SiO2, heptane/ethyl acetate 98:2) to yield 0.40 g of (2-cyclopropyl-phenyl)-acetonitrile as a light-yellow oil that was used directly for the next step.

후처리

  1. customThe solvent was evaporated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified

출처 및 근거

ORD 기록
ord-4d171b5178dd4365b39a40fdf193045c
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875645B2

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