1,2-Dimethoxyethane → 3,5-Dimethyl-4-[2-(methyloxy)-5-nitrophenyl]isoxazole

HRID 1042997

Reaktionsgleichung

Reaktionsgleichung von HRID 1042997
I[C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH3:13][C:14]1[C:18](B(O)O)=[C:17]([CH3:22])[O:16][N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC>C(OCC)(=O)C.O>[CH3:13][C:14]1[C:18]([C:2]2[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[CH:6][C:7]=2[O:8][CH3:9])=[C:17]([CH3:22])[O:16][N:15]=1

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 948062-Iodo-1-methoxy-4-nitrobenzeneHCID 27343463,5-Dimethylisoxazole-4-boronic acid

Produkt 1

HCID 574655703,5-Dimethyl-4-[2-(methyloxy)-5-nitrophenyl]isoxazoleAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

3-Iodo-4-(methoxy) nitrobenzene (65 g, 233 mmol, Matrix Scientific), (3,5-dimethyl-4-isoxazolyl)boronic acid (36.1 g, 256 mmol) and cesium carbonate (152 g, 466 mmol) were combined with DME (80 ml) and water (40 ml) and the mixture was degassed with nitrogen for 10 min, then PEPPSI™ catalyst (3.96 g, 5.82 mmol) was added and the mixture heated at 90° C. for 4 h, then cooled and diluted with ethyl acetate (800 ml). The resulting suspension was filtered through Celite and the filtrate washed with water (2×500 ml). The solvent was dried (sodium sulphate), filtered and evaporated to give a brown solid which was triturated with ether (30 ml). The solid product was washed with ether (100 ml) to give 3,5-dimethyl-4-[2-(methyloxy)-5-nitrophenyl]isoxazole as beige solid (48.2 g).

Aufarbeitung

  1. customthe mixture was degassed with nitrogen for 10 min
  2. temperaturecooled
  3. filtrationThe resulting suspension was filtered through Celite
  4. washthe filtrate washed with water (2×500 ml)
  5. dry with materialThe solvent was dried (sodium sulphate)
  6. filtrationfiltered
  7. customevaporated
  8. customto give a brown solid which
  9. customwas triturated with ether (30 ml)
  10. washThe solid product was washed with ether (100 ml)

Quellen und Nachweise

ORD-Eintrag
ord-f92accf7167c4fe5bdab9d8575060449
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557984B2

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