Dimethylformamide → 3-(Difluoromethoxy)benzaldehyde

HRID 1042629

Reaktionsgleichung

Reaktionsgleichung von HRID 1042629
[O:1]=[C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4]N1.Cl[C:11]([F:16])([F:15])C([O-])=O.[Na+].[CH3:18]N(C=O)C>C(#N)C.C(OCC)(=O)C>[F:15][CH:11]([F:16])[O:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][CH:18]=1)[CH:8]=[O:9]

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 15126692-Hydroxy-4-pyridinecarboxaldehydeHCID 2734985Sodium chlorodifluoroacetate

Produkt 1

HCID 27369853-(Difluoromethoxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-oxo-1,2-dihydropyridine-4-carbaldehyde (1.72 g, 11.3 mmol) in 25 mL of acetonitrile was added sodium chlorodifluoroacetate (0.925 g, 7.51 mmol). The reaction was heated to reflux under an atmosphere of nitrogen for 15 h, and then DMF (3 mL) was added. The mixture was heated to 100° C. for 3 d, cooled to rt, and diluted with ethyl acetate. The organic solution was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 3-(difluoromethoxy)benzaldehyde.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux under an atmosphere of nitrogen for 15 h
  3. temperaturecooled to rt
  4. washThe organic solution was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-de68ac8e0ea145089587f8be7584033d
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557992B2

Verknüpfte Notizen

Wird geladen…