Catechol → o-(5-Fluoro-2-nitrophenoxy)phenol

HRID 21520

Reaktionsgleichung

Reaktionsgleichung von HRID 21520
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C(=O)([O-])[O-].[K+].[K+].F[C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24]>C(#N)C.[Cl-].[Na+].O.C(Cl)Cl>[F:22][C:20]1[CH:19]=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[C:16]([CH:21]=1)[O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4]

Komponenten

7

Edukt 3

HCID 289CatecholHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

Produkt 1

HCID 19932387o-(5-Fluoro-2-nitrophenoxy)phenolAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
28 °C

Versuchsvorschrift

Catechol (103.8 g, 0.94 mol) and potassium carbonate (129.9 g, 0.94 mol) are added to a solution of 2,4-difluoronitrobenzene (50.0 g, 0.314 mol) in acetonitrile. The reaction mixture is stirred at 28° C. for 24 hours, poured into brine and extracted with ether. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a brown gum. Flash chromatography of the gum using silica gel and a 10% hexanes in methylene chloride solution gives the title product as a yellow solid (43 g) which is identified by 1HNMR spectral analysis.

Aufarbeitung

  1. extractionextracted with ether
  2. extractionThe organic extract
  3. washis washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a brown gum

Quellen und Nachweise

ORD-Eintrag
ord-3ac0287e59ea458f9d86f75740575bec
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424280

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