Iodine → 6-Chloro-2-iodo-1-methyl-1H-indole

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Reaction Steps

A solution of 6-chloro-l-methylindole (0.83 g, 5.0 mmole) in diethyl ether is treated with 1.7 M t-butyl lithium in hexanes (3.5 mL, 6.0 mmole) at 0° C., stirred at ambient temperatures for 0.25 hour, treated with I2 (1.52 g, 6.0 mmole), stirred at room temperature until reaction is complete by TLC analysis, treated with aqueous sodium sulfite and extracted with diethyl ether. The combined ether extracts are dried over MgSO4 and concentrated in vacuo to afford the title product as a brown solid, 1.52 g (contains ether). The product is used as is in Example 9.

Provenance & Evidence