Ethyl Acetate → 4-(Difluoromethoxy)benzonitrile

HRID 3017

Reaktionsgleichung

Reaktionsgleichung von HRID 3017
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].Cl[C:11]([F:16])([F:15])C([O-])=O.[Na+].[OH-].[Na+].C(OCC)(=O)C>CN(C=O)C>[F:15][CH:11]([F:16])[O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 130194-CyanophenolHCID 14798Sodium HydroxideHCID 2734985Sodium chlorodifluoroacetate

Produkt 1

HCID 27369904-(Difluoromethoxy)benzonitrileAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Cyanophenol (0.50 g, 4.2 mmol, Aldrich), sodium chlorodifluoroacetate (0.77 g, 5 mmol, Alfa Products), and sodium hydroxide (0.20 g, 5 mmol) were combined in dry DMF (2 mL) under an atmosphere of argon. After stirring at 125°-130° C. for 5 h, the mixture was cooled to RT, ethyl acetate (50 mL) was added and the organic layer was washed twice with brine. The organic extract was dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes) to provide a white solid. The solid was sublimed (1 mm Hg, 23° C.) to provide the title compound as colorless crystals (0.29 g, 41%). mp 33°-35° C.

Aufarbeitung

  1. washthe organic layer was washed twice with brine
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes)
  7. customto provide a white solid
  8. custom(1 mm Hg, 23° C.)

Quellen und Nachweise

ORD-Eintrag
ord-9878f8a1a69f4990b1191065d489c660
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731477

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