Halogenation of 1-substituted skatoles. Preparation of 3-bromomethylindoles.

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Halogenation of skatole (1a) and 1-acetyl (1b), 1-benzenesulfonyl (1c), and 1-tosylskatole (1d) with N-bromosuccinimide (NBS) N-chlorosuccinimide (NCS), N-iodosuccinimide (NIS) in acetic acid or carbon tetrachloride has been studied. Bromination of 1a with NBS in carbon tetrachloride in the presence of benzoyl peroxide yielded 2-bromoskatole (2a) in 85% yield. reaction of 1b with NBS (NCS) in acetic acid or in carbon tetrachloride yielded 1-acetyl-2-(1-acetyl-3-indolylmethyl)-3-methylindole (7b) and 2-halo derivative (2b). The reaction of 2b (X=Br) with skatole or 3-methyloxindole gave 1-acetylskatole (1b). Bromination of 1c (1d) with NBS in carbon tetrachloride yielded 3-bromomethyl derivative (6c or 6d). On the other hand the reaction of (1c or 1d) with NBS in acetic acid gave 2-bromo derivative (2c or 2d) and the 3-bromo-oxindole (5c or 5d). Mechanism of the formation of 7b and other products has been discussed.

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