Chlorosuccinimide → 6-{[tert-Butyl(dimethyl)silyl]oxy}-3-chloro-1H-indole

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Reaction Steps

A solution of N-chlorosuccinimide (270 mg, 2 mmol) in dichloromethane (4 ml) is added within 30 min to a solution of 6-(tert-butyl-dimethyl-silanyloxy)-1H-indole (500 mg, 2 mmol) in dichloromethane (10 ml) at 0° C. under an argon atmosphere. The solution was naturally warmed to ambient temperature and stirred for 2 h. Ice water was added and the mixture was extracted two times with tert-butyl methyl ether. The combined extracts were dried over sodium sulfate and the solvent was removed under reduced pressure to give 560 mg (1.98 mmol, 98%) of the title compound as red solid which was used in the next step without further purification.

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