Water → 5-(3-Fluorophenoxy)thiophene-2-carbonitrile

HRID 2080065

Reaktionsgleichung

Reaktionsgleichung von HRID 2080065
[N+]([C:4]1[S:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=1)([O-])=O.[F:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(OCC)(=O)C>[F:11][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][C:4]1[S:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 5192945-Nitrothiophene-2-carbonitrile

Produkt 1

HCID 231306135-(3-Fluorophenoxy)thiophene-2-carbonitrileAusbeute 23,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-Nitrothiophene-2-carbonitrile (2 g, 13 mmol), 3-fluorophenol (1.75 g, 15.6 mmol) and potassium carbonate (3.6 g, 26 mmol) were suspended in dimethylsulfoxide (15 mL), and the mixture was stirred at room temperature for 16 hours. Water and ethyl acetate were added for partitioning, silica gel was added to the organic layer, and the solvent was evaporated in vacuo for adsorption. Purification was carried out by silica gel column chromatography (hexane:ethyl acetate=10:1), and the title compound (670 mg, 3.1 mmol, 23.5%) was obtained as an oil.

Aufarbeitung

  1. customfor partitioning
  2. additionsilica gel was added to the organic layer
  3. customthe solvent was evaporated in vacuo for adsorption
  4. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-a94c4a9e167146c893a6bacce3f2f810
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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