Thionyl Chloride → 5-(4-Chloro-2-methoxyphenyl)naphthalene-2-sulfonyl chloride
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:18]([O-])(=[O:20])=[O:19])=[CH:13]3)=[C:4]([O:22][CH3:23])[CH:3]=1.[Na+].S(Cl)([Cl:27])=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:18]([Cl:27])(=[O:20])=[O:19])=[CH:13]3)=[C:4]([O:22][CH3:23])[CH:3]=1Komponenten
3
Versuchsvorschrift
A round bottom flask was charged with sodium 5-(4-chloro-2-methoxyphenyl)naphthalene-2-sulfonate (0.137 g, 0.369 mmol) and a septum was attached and the flask flushed with N2. DMF (1.232 mL) was added followed by thionyl chloride (0.081 mL, 1.108 mmol) by syringe at rt, an exotherm was observed. The solution was maintained at rt for 1 h, and then poured into a separatory funnel containing ice. The resulting mixture was extracted with DCM (2×15 mL). The combined organic layers were washed with water (2×10 mL) and brine (1×10 mL) and dried over Na2SO4 and concentrated to give 5-(4-chloro-2-methoxyphenyl)naphthalene-2-sulfonyl chloride (0.121 g, 0.329 mmol), which was used immediately without further purification.
Aufarbeitung
- customthe flask flushed with N2
- additionDMF (1.232 mL) was added
- additionpoured into a separatory funnel
- additioncontaining ice
- extractionThe resulting mixture was extracted with DCM (2×15 mL)
- washThe combined organic layers were washed with water (2×10 mL) and brine (1×10 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-ed8e263e38784056a24f2134f36fa0c4
- Quelldatensatz
- uspto-grants-2015_04
- Patentnummer
- US09012443B2
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