4-Hydroxybenzaldehyde → HCID 59730014, Verbindung

HRID 130732

Reaktionsgleichung

Reaktionsgleichung von HRID 130732
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:18]=[C:17](F)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Cl:10][C:11]1[CH:18]=[C:17]([O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 1090002-Chloro-4-fluorobenzonitrile

Produkt 1

HCID 59730014HCID 59730014, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Hydroxy benzaldehyde (1 equiv), 2-chloro-4-fluorobenzonitrile (1 equiv) and K2CO3 (2.5 equiv) in anhydrous DMF (0.2 M) were heated at 110° C. under nitrogen during 1 hour (the reaction can be monitored by tlc). After cooling down to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum (toluene was added to aid DMF evaporation). The crude mixture was purified by flash chromatography using hexanes/ethyl acetate (4:1) as eluent.

Aufarbeitung

  1. customthe reaction
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum (toluene was added to aid DMF evaporation)
  6. customThe crude mixture was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d284882dfca44239b0836b3ccd0b53d2
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381719B2

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