Iodine → 5-chloro-2-iodo-1-methyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-chloro-1-methylindole (10.0 g, 60.4 mmole) and n-butyl lithium (29 mL of 2.5 M sol'n in hexanes, 72.5 mmole) in diethyl ether is heated at reflux temperature for 3 hours, cooled to 0° C., treated with iodine (18.4 g, 72.5 mmole), stirred at 0° C. for 1 hour, warmed to room temperature, stirred for 1 hour, and treated with aqueous sodium sulfite. After phase separation, the organic phase is dried over MgSO4 and concentrated in vacuo to give the title product as a brown oil which solidified on standing, 16.5 g (93.7% yield). The title product is used as in Example 4.

Provenance & Evidence