Abstract
Reaction of 3-tert-butylindole (1a) with NBS in acetic acid gave 3-tert-butyloxindole (2a) and 6-bromo-3-tert-butylindole (3a) instead of 2-bromo derivative (5a). Reactions of 1-acetyl-(1b) and 1-tert-butyl-(1c) derivatives under similar conditions gave 3-bromooxindole (6b) and the brominated indole (7) respectively. On the other hand reaction of 1a with NBS in boiling carbon tetrachloride in the presence of benzoyl peroxide gave unstable 5a as a main product. Reaction of 1b under similar condition did not proceed, but 1c gave 7 as a main product.
