Thiophenol → 4-Bromo-N-methyl-2-nitro-3-(phenylthio)aniline
Reaktionsgleichung
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1F.C(=O)([O-])[O-].[Cs+].[Cs+].[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[S:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
A solution of 4-bromo-3-fluoro-N-methyl-2-nitroaniline (0.30 g, 1.20 mmol) in N,N-dimethylformamide (2.45 mL) was treated with cesium carbonate (0.472 g, 1.45 mmol) and benzenethiol (0.149 mL, 1.45 mmol). The resultant reaction mixture was warmed to 80° C. and stirred at 80° C. for 30 min, after which time the reaction mixture was diluted with ethyl acetate and water. Layers were separated and the organic layer was washed with 10% solution of K2CO3 and brine, dried with sodium sulfate, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (100% hexanes to 40% EtOAc/hexanes) gave the desired product (396 mg, 97%) as an orange solid. LCMS calculated for C13H12BrN2O2S (M+H)+: m/z=339.0, 341.0. found: 338.9, 340.9.
Aufarbeitung
- customThe resultant reaction mixture
- customLayers were separated
- washthe organic layer was washed with 10% solution of K2CO3 and brine
- dry with materialdried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give the crude product
- customPurification by flash column chromatography (100% hexanes to 40% EtOAc/hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-d8231d3e86734e1ba0f561fc87a9402c
- Quelldatensatz
- uspto-grants-2016_07
- Patentnummer
- US09399640B2
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