Reaktion #7950

Reaktionsgleichung

N-Chlorosuccinimide

2-butyl-5-methoxy-1-indanone

→

2-butyl-4-chloro-5-methoxy-1-indanone

Ausbeute 15.4%

Lösungsmittel

EtOAc

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 5% aqueous NaHCO3 (20 ml), water (3×50 mL) and brine (10 mL)
2. 2
   Trocknendried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Sonstigeevaporated under vacuum
5. 5
   SonstigeThe residue was purified by column chromatography on EM silica gel 60 (2320-400 mesh, 2.75×29 cm)
6. 6
   Wascheneluting with CH2Cl2

Vorschrift

N-Chlorosuccinimide (505 mg, 3.8 mmol) was added to a solution of 2-butyl-5-methoxy-1-indanone (825 mg, 3.8 mmol) in anhydrous dimethylformamide (3.8 mL) and the resulting solution was stirred under nitrogen and at room temperature overnight. The reaction mixture was diluted with EtOAc (50 mL), washed with 5% aqueous NaHCO3 (20 ml), water (3×50 mL) and brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by column chromatography on EM silica gel 60 (2320-400 mesh, 2.75×29 cm), eluting with CH2Cl2, to afford 2-butyl-4-chloro-5-methoxy-1-indanone (148 mg) as an oil.

Quelle