Réaction #7950

Équation de réaction

N-Chlorosuccinimide

2-butyl-5-methoxy-1-indanone

→

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

Rendement 15.4%

Solvants

EtOAc

dimethylformamide

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source