Reaktionsgleichung
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([N+:13]([O-:15])=[O:14])[CH:7]=1)(=[O:4])=[O:5])[CH3:2]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
To a solution of 1-(ethylsulfonyl)-4-fluorobenzene (1.36 mmol, 0.257 g) in sulfuric acid (1.32 ml) was added potassium nitrate (0.243 g) at 80° C. The mixture was stirred at 90° C. for 2 hours. Ice water (5 ml) was added and the mixture was extracted with ethyl acetate (25 ml) and washed with water (20 ml) and brine (10 ml). The organic extracts were combined and dried over sodium sulfate and concentrated. The residue was purified by column chromatography (hexane/ethylacetate 1:3) to give a light yellow solid which was crystallized from methanol. HPLC indicated 98% purity, mp 128-131° C., (0.21 g, 66% yield). 1H NMR (CDCl3): 1.35 (t, 3H, CH3), 3.21 (q, 2H, CH2), 7.55 (t, 1H, Ar—H), 8.21 (m, 1H, Ar—H), 8.64 (d, 1H, Ar—H); MS: 229 M−. Elemental Analysis (C, H, N, F, S) for C8H8FNO4S; calculated C, 41.20; H, 3.46; N, 6.01; F, 8.15; S, 13.75. found C, 41.31; H, 3.35; N, 5.85; F, 8.17; S, 13.53.
Aufarbeitung
- extractionthe mixture was extracted with ethyl acetate (25 ml)
- washwashed with water (20 ml) and brine (10 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe residue was purified by column chromatography (hexane/ethylacetate 1:3)
- customto give a light yellow solid which
- customwas crystallized from methanol
Quellen und Nachweise
- ORD-Eintrag
- ord-f71feadad67f41ecaa39e431e9b6e979
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08541476B2
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