4-Nitrophenol → 4-(Difluoromethoxy)nitrobenzene

HRID 3020

Reaktionsgleichung

Reaktionsgleichung von HRID 3020
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:12]([F:18])([F:17])C(OC)=O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[F:17][CH:12]([F:18])[O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 9804-NitrophenolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 73935Methyl chlorodifluoroacetate

Produkt 1

HCID 27370144-(Difluoromethoxy)nitrobenzeneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Nitrophenol (0.14 g, 1.0 mmol, Aldrich), methyl chlorodifluoroacetate (0.29 g, 2.0 mmol, Aldrich) and potassium carbonate (0.29 g, 2.1 mmol) were combined in dry DMF (0.5 mL) under an argon atmosphere. After stirring at 95°-100° C. for 0.5 h, the mixture was cooled to RT, ethyl acetate (20 mL) was added and the organic layer was washed three times with 10% NaOH. The organic extract was dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 20% ether/hexanes) to provide the title compound as a white solid (0.12 g, 65%). mp 33°-35° C.

Aufarbeitung

  1. washthe organic layer was washed three times with 10% NaOH
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (silica gel, 20% ether/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-78322038f273421dabe49798105b950a
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731477

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