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

HRID 2080065

Reaction equation

HRID 2080065 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 231306135-(3-Fluorophenoxy)thiophene-2-carbonitrileYield 23.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-a94c4a9e167146c893a6bacce3f2f810
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Linked notes

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