Water → 3,5-Dimethyl-4-[2-(methyloxy)-5-nitrophenyl]isoxazole

HRID 1042974

반응식

HRID 1042974 반응식
I[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].[OH2:13]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:7][C:6]1[C:5]([C:2]2[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=2[O:11][CH3:12])=[C:4]([CH3:3])[O:13][N:8]=1

참가 물질

5

반응물 2

HCID 962WaterHCID 948062-Iodo-1-methoxy-4-nitrobenzene

생성물 1

HCID 574655703,5-Dimethyl-4-[2-(methyloxy)-5-nitrophenyl]isoxazole

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

To a solution of 2-iodo-1-(methoxy)-4-nitrobenzene (2 g, 7.17 mmol, 1 eq.) and (3,5-dimethylisoxazole)boronic acid (3.03 g, 21.5 mmol, 3 eq.) in DME (44 ml) and water (7 ml) were added tetrakis(triphenylphosphine) palladium(0) (0.415 g, 0.05 eq.) and Ba(OH)2.8H2O (4.52 g, 14.33 mmol, 2 eq.). The mixture was heated at 80° C. for 16 h. To complete the reaction (3,5-dimethylisoxazole)boronic acid (1 eq.) was added and the mixture was heated for 4 h. The cooled mixture was filtered and extracted with DCM. The organic phase was washed with saturated aqueous Sodium hydrogen carbonate and water, dried over Na2SO4 and filtered. Evaporation of the solvent in vacuo gave a crude oil which was precipitated with iPr2O to afford the title compound as a rust solid (1.735 g, 97%). GC/MS m/z: 248

후처리

  1. additionwas added
  2. temperaturethe mixture was heated for 4 h
  3. filtrationThe cooled mixture was filtered
  4. extractionextracted with DCM
  5. washThe organic phase was washed with saturated aqueous Sodium hydrogen carbonate and water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customEvaporation of the solvent in vacuo
  9. customgave a crude oil which
  10. customwas precipitated with iPr2O

출처 및 근거

ORD 기록
ord-9627abbc5c084564a3c54a62c1fb227f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557984B2

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