Dimethylformamide → 3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

HRID 16328

Reaktionsgleichung

Reaktionsgleichung von HRID 16328
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1F)[CH:22]=[O:23]>O.C(OCC)(=O)C>[F:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1)[CH:22]=[O:23]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5880883,4-DifluorobenzaldehydeHCID 178418800HCID 178418800, Verbindung

Produkt 1

HCID 707008423-Fluoro-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeAusbeute 17,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

4-Methylimidazole (46.4 g) and potassium carbonate (78.0 g) were added to a DMF solution (533 mL) of 3,4-difluorobenzaldehyde (40.0 g) at room temperature. This reaction solution was stirred at 90° C. for 6 hr and then was allowed to cool to room temperature. To the reaction solution, ethyl acetate and water were added. The organic layer was separated, washed with saturated saline, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system) and further solidified with tert-butylmethylether to give 10.1 g of the title compound. The physical property values of this compound were as follows:

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customThe organic layer was separated
  3. washwashed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system) and further solidified with tert-butylmethylether

Quellen und Nachweise

ORD-Eintrag
ord-c7bc762f2f1545c5a7b5de280b391cda
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737141B2

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