Phenol → Ethyl 5-amino-2-phenoxybenzoate

HRID 1925936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1925936
F[C:2]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:13][C:10]1[CH:11]=[CH:12][C:2]([O:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:3]([CH:9]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

5

Edukt 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 12793176Ethyl 2-fluoro-5-nitrobenzoate

Produkt 1

HCID 53848249Ethyl 5-amino-2-phenoxybenzoateAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of ethyl 2-fluoro-5-nitrobenzoate (1.07 g), phenol (565 mg), potassium carbonate (1.38 g) and N,N-dimethylformamide (20 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=20:80→30:70). The object fraction was concentrated under reduced pressure and ethanol (20 mL) and 10% palladium on carbon (1.5 g) were added to the residue (1.54 g). The mixture was stirred overnight under a hydrogen stream. The catalyst was filtered off, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=20:80→50:50) and recrystallized from diisopropyl ether-hexane to give the title compound (1.07 g) as a pale-brown powder.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=20:80→30:70)
  8. concentrationThe object fraction was concentrated under reduced pressure and ethanol (20 mL) and 10% palladium on carbon (1.5 g)
  9. additionwere added to the residue (1.54 g)
  10. stirringThe mixture was stirred overnight under a hydrogen stream
  11. filtrationThe catalyst was filtered off
  12. concentrationthe filtrate was concentrated
  13. customThe obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=20:80→50:50)
  14. customrecrystallized from diisopropyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0d0579026d814624b809b1c009ca693a
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178543B2

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