Dimethyl Sulfoxide → 5-(4-Fluorophenoxy)thiophene-2-carbonitrile

HRID 78059

Reaktionsgleichung

Reaktionsgleichung von HRID 78059
CS(C)=O.[N+]([C:8]1[S:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=1)([O-])=O.[F:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>O>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:8]2[S:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=2)=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 5192945-Nitrothiophene-2-carbonitrile

Produkt 1

HCID 231305625-(4-Fluorophenoxy)thiophene-2-carbonitrileAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a dimethyl sulfoxide (100 mL) solution of 5-nitro-2-thiophene carbonitrile (5.00 g, 32.4 mmol) were added 4-fluorophenol (5.45 g, 48.6 mmol) and potassium carbonate (11.2 g, 81.0 mmol) under nitrogen atmosphere, which was stirred for 16 hours at 60° C. The reaction solution was cooled to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:10→1:5) to obtain the title compound (6.10 g, 85.9%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:10→1:5)

Quellen und Nachweise

ORD-Eintrag
ord-e032a5b32a4a429b9fe270faaaf34eb1
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

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