Water → 4-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde

HRID 1962566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1962566
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=1.[Cl:15]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:15][C:9]1[C:10]([CH:13]=[O:14])=[CH:11][NH:12][C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Komponenten

5

Edukt 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 469085935-(2-Fluorophenyl)-1H-pyrrole-3-carboxaldehyde

Produkt 1

HCID 866309734-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehydeAusbeute 46,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution (15 mL) of 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (1.0 g) in N,N-dimethylformamide was added N-chlorosuccinimide (0.71 g) at 0° C., and the mixture was stirred at 60° C. for 2 hr. The mixture was cooled to room temperature, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=8:1→3:1) to give the title compound as a yellow powder (yield 0.55 g, 46%).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=8:1→3:1)

Quellen und Nachweise

ORD-Eintrag
ord-c83eb50a6d81490790999f8b0d1dc2e1
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415368B2

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