Reacción #51657

Ecuación de reacción

N-chlorosuccinimide

Diethyl ether

2-methylindole

Dimethylsulfide

→

(2-methyl-1H-indol-3-yl)-dimethylsulfonium chloride

Disolventes

dichloroethane

dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas replaced by a dry-ice acetone bath
2. 2
   Otrowas lowered to −50° C
3. 3
   workup.STIRRINGwith stirring
4. 4
   workup.STIRRINGThe reaction mixture was stirred
5. 5
   workup.WAITto reach 20° C. over about an hour
6. 6
   workup.STIRRINGwith stirring
7. 7
   Otrothe precipitate which formed
8. 8
   Filtraciónwas filtered
9. 9
   Lavadowashed well with ether
10. 10
    Otrodried overnight in a vacuum oven at room temperature

Procedimiento

N-chlorosuccinimide (3.85 g, 29.35 mmole) was suspended in dichloroethane (40 ml) under a nitrogen atmosphere and cooled to −10° C. using an ice-salt-acetone bath. Dimethylsulfide (3 ml) was slowly added with stirring over a period of about 5 minutes. The mixture was stirred at this temperature for 10 minutes beyond the addition, at which time the ice-salt-acetone bath was replaced by a dry-ice acetone bath and the temperature was lowered to −50° C. To this solution was added 2-methylindole (3.85 g, 29.35 mmole) dissolved in dichloroethane (40 ml) slowly with stirring. The reaction mixture was stirred while allowing the temperature to reach 20° C. over about an hour. Diethyl ether (90 ml) was added with stirring and the precipitate which formed was filtered, washed well with ether, and dried overnight in a vacuum oven at room temperature. The free-flowing powder of (2-methyl-1H-indol-3-yl)-dimethylsulfonium chloride thus obtained was used without further purification in the following step.

Fuente