Water → 2-(4-Nitrophenyl)-4-(2-fluoroethoxy)benzothiophene

HRID 454802

Reaktionsgleichung

C(=O)([O-])[O-].[K+].[K+].CS([O:11][CH2:12][CH2:13][F:14])(=O)=O.[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[S:25][C:26]3[CH:32]=[C:31](O)[CH:30]=[CH:29][C:27]=3[CH:28]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16].O>CN(C)C=O>[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[S:25][C:26]3[CH:32]=[CH:31][CH:30]=[C:29]([O:11][CH2:12][CH2:13][F:14])[C:27]=3[CH:28]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Potassium carbonate (611 mg, 4.42 mmol) and 2-fluoroethyl methane sulfonate (FCH2CH2OMs, 251 mg, 1.77 mmol) were added to 2-(4-nitrophenyl)-6-hydroxybenzothiophene (1-4, 400 mg, 1.47 mmol) obtained in Example 4 dissolved in a solution of dimethylformamide (DMF, 100 mL), heated at 80° C. for 8 hours, cooled to room temperature, followed by adding water. The resulting product was extracted with ethyl acetate, evaporated after a treatment with sodium sulfate under reduced pressure. Purification was performed by column chromatograph to give the target compound 2-(4-nitrophenyl)-4-(2-fluoroethoxy)benzothiophene (1-5, 224 mg, 48%) as a yellow solid. The obtained target compound 1-5 had a melting point of 176.5-178.0° C., and the following physical data;

Aufarbeitung

customobtained in Example 4
temperaturecooled to room temperature
extractionThe resulting product was extracted with ethyl acetate
customevaporated after a treatment with sodium sulfate under reduced pressure
customPurification

Quellen und Nachweise

ORD-Eintrag: ord-38707b8be6cb411bb65aff9360afd226
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08497260B2

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