Реакция #51663

Уравнение реакции

1-methylsulfanyl-propan-2-one

2-chloroaniline

triethylamine

t-butyl hypochlorite

→

7-Chloro-2-methyl-3-methylsulfanyl-1H-indole

Растворители

dichloromethane

dichloromethane

dichloromethane

dichloromethane

Water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   workup.ADDITIONwas added
3. 3
   workup.ADDITIONUpon completion of the addition
4. 4
   Другоеto reach ambient temperature
5. 5
   Другоеthe layers were separated
6. 6
   Сушкаthe organic layer was dried over magnesium sulfate
7. 7
   Фильтрацияfiltered
8. 8
   Другоеthe solvent evaporated to dryness
9. 9
   ДругоеThe residue was purified by column chromatography on silica gel using
10. 10
    workup.ADDITIONa mixture of hexane-ethyl acetate (95:5)
11. 11
    Промывкаto elute 7-chloro-2-methyl-3-methylsulfanyl-1H-indole (1.94 g) as an oil

Методика

Using the procedure described in J. Amer. Chem. Soc., 1974, 96 (17) 5495 , 2-chloroaniline (1.27 g, 10 mmole) was dissolved in dichloromethane (35 ml) and cooled to −65° C. To this solution was added dropwise with vigorous stirring, t-butyl hypochlorite (1.08 g, 10 mmole) in dichloromethane (5 ml). After 10 minutes 1-methylsulfanyl-propan-2-one (1.04 g, 10 mmole) dissolved in dichloromethane (5 ml) was added. The mixture was stirred at −65° C. for 1 h more. At this point triethylamine (1.01 g, 10 mmole) dissolved in dichloromethane (5 ml) was added. Upon completion of the addition, the reaction mixture was allowed to reach ambient temperature. Water was added and the layers were separated, the organic layer was dried over magnesium sulfate, filtered and the solvent evaporated to dryness. The residue was purified by column chromatography on silica gel using a mixture of hexane-ethyl acetate (95:5) to elute 7-chloro-2-methyl-3-methylsulfanyl-1H-indole (1.94 g) as an oil.

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