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

HRID 1042974
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1042974
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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9627abbc5c084564a3c54a62c1fb227f
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08557984B2

Notizen zur Reaktion

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