Cesium carbonate → HCID 21930430, Verbindung

HRID 1178495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178495
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.[OH:12][C:13]1[C:14]([O:21][CH3:22])=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:12][C:13]2[CH:20]=[CH:19][CH:18]=[C:15]([CH:16]=[O:17])[C:14]=2[O:21][CH3:22])[CH:3]=1

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 112753024-Chloro-2,5-difluorobenzonitrileHCID 118049533-Hydroxy-2-methoxybenzaldehyde

Produkt 1

HCID 21930430HCID 21930430, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Chloro-2,5-difluorobenzonitrile (0.45 g, 2.6 mmol), 3-hydroxy-2-methoxybenzaldehyde (0.39 g, 2.6 mmol) and cesium carbonate (0.84 g, 2.6 mmol) were heated with stirring in dry DMF (5 mL) at 50° C. for 18 h. The reaction mixture was cooled, poured into 0.1N sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate layer was separated, washed with 0.1N sodium hydroxide solution (1×), water (2×), brine (1×), and dried over MgSO4. After filtration, the solvent was removed in vacuo, and purified by chromatography to yield 4-chloro-5-fluoro-2-(3-formyl-2-methoxyphenoxy)benzonitrile (0.33 g, 42%) as a pale yellow solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with 0.1N sodium hydroxide solution (1×), water (2×), brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo
  8. custompurified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-75f68b61a8a44ed499582993608be397
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276528B2

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