Methyl iodide → 4-Chloro-1-methyl-1H-indole

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A mixture of 60 g of 4-chloro-1H-indole, 400 ml of benzene, 200 ml of 50% sodium hydroxide solution, 68 g of n-tetrabutylammonium hydrogen sulfate and 68 ml of methyl iodide was stirred at 40° C. for 4 hours and was then cooled. The decanted aqueous phase was extracted with ethyl acetate and the combined organic phases were washed with aqueous sodium chloride, dried over magnesium sulfate and distilled to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-2 cyclohexanebenzene mixture to obtain 63.85 g of 1-methyl-4-chloro-1H-indole.

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