Sodium hydride → 3-Fluoro-4-(3-cyano-1-pyrrolyl)nitrobenzene

HRID 1167464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1167464
[C:1]([C:3]1[CH:7]=[CH:6][NH:5][CH:4]=1)#[N:2].[F:8][C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][C:14]=1F.[H-].[Na+]>CN(C=O)C>[F:8][C:9]1[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[CH:12]=[CH:13][C:14]=1[N:5]1[CH:6]=[CH:7][C:3]([C:1]#[N:2])=[CH:4]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 5642063-Cyanopyrrole

Produkt 1

HCID 229960033-Fluoro-4-(3-cyano-1-pyrrolyl)nitrobenzeneAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Cyanopyrrole (3.6 g, 39.1 mmol , CE Loader et al, Can. J. Chem., 1981, 59, 2673) and 3,4-difluoronitrobenzene (6.5 g, 40.9 mmol) were dissolved in DMF (50 ml) and cooled in an ice-bath. The mixture was stirred and sodium hydride (60% in oil, 1.6 g, 40 mmol) added over 20 minutes. After allowing the mixture to come to ambient temperature, it was heated to 650 for 1 hour. Solvent was evaporated, the residue triturated with water, and filtered. The crude solide was purified by flash chromatography on silica, eluting with dichloromethane. Relevant fractions were combined to give the title product (3.75 g), mp 117-119°.

Aufarbeitung

  1. temperaturecooled in an ice-bath
  2. customto come to ambient temperature
  3. temperatureit was heated to 650 for 1 hour
  4. customSolvent was evaporated
  5. customthe residue triturated with water
  6. filtrationfiltered
  7. customThe crude solide was purified by flash chromatography on silica
  8. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-de1496b6d1de429cb8e694e59e338108
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06617339B1

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