Water → 5-(4-Fluorophenoxy)thiophene-2-carbonitrile

HRID 2080070Notes

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:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(OCC)(=O)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:4]2[S:8][C:7]([C:9]#[N:10])=[CH:6][CH:5]=2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

5-Nitrothiophene-2-carbonitrile (2.0 g, 13 mmol), 4-fluorophenol (2.9 g, 26 mmol) and potassium carbonate (5.4 g, 39 mmol) were suspended in dimethylsulfoxide (30 mL), and the mixture was stirred for 30 minutes at 60° C. Water and ethyl acetate were added to the reaction mixture, which was then separated, the organic layer was washed with water twice, then, NH silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purification was carried out by NH silica gel column chromatography (hexane:ethyl acetate=20:1), and the title compound (3.7 g, containing 4-fluorophenol) was obtained as a brown oil.

Workup

customwas then separated
washthe organic layer was washed with water twice
additionNH silica gel was added to the organic layer
customthe solvent was evaporated in vacuo for adsorption, purification

Sources & evidence

ORD record: ord-2ecc6ab6c82148ba96d5a4a050bc1d57
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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