Reaktionsgleichung
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:9]1[CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:13][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>[Cu]I.CN(C=O)C>[C:1]1([S:7][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A mixture of thiophenol (1.0 g, 9.1 mmol), 3-iodonitrobenzene (1.9 g, 7.6 mmol), CuI (0.14 g, 0.76 mmol), K2CO3 (1.67 g, 12.1 mmol), and DMF (10 mL) was heated to 100° C. in a flame-dried sealed tube for 16 h. The mixture was allowed to cool and was poured over ice. The resulting mixture was extracted with EtOAc (2×), and the organic extracts were combined and washed sequentially with equal volumes of aqueous 1M HCl, water, and aqueous 1M NaOH. The solution was dried, concentrated, and the residue was purified by FCC (100:0 to 95:5 hexanes/EtOAc) to provide the titled compound, which was contaminated with ca. 10% thiophenol (1.43 g), and was taken on to subsequent steps without further purification.
Aufarbeitung
- customsealed tube for 16 h
- temperatureto cool
- additionwas poured over ice
- extractionThe resulting mixture was extracted with EtOAc (2×)
- washwashed sequentially with equal volumes of aqueous 1M HCl, water, and aqueous 1M NaOH
- customThe solution was dried
- concentrationconcentrated
- customthe residue was purified by FCC (100:0 to 95:5 hexanes/EtOAc)
Quellen und Nachweise
- ORD-Eintrag
- ord-0bcc46a1b38348919cfa06ce86502a56
- Quelldatensatz
- uspto-grants-2015_01
- Patentnummer
- US08937078B2
Verknüpfte Notizen
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