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

HRID 1042974

反応式

HRID 1042974 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-9627abbc5c084564a3c54a62c1fb227f
出典データセット
uspto-grants-2013_10
特許番号
US08557984B2

関連ノート

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