A series of tetramethyl 1-substituted benzyl-3a,7a-dihydro-1H-indole-2,3,3a,4-tetracarboxylates were prepared and their reactions with bromine were examined. The initial reaction seemed to be the formation of the intermediate N-bromo quaternary ammonium bromide. This intermediate underwent aromatization with loss of the 3a-methoxycarbonyl group. Bromine replaced the N-substituent of the p-methoxybenzyl compound and addition of bromine occurred across the $C_6-C_7$ double bond of the indole ring. Bromination of the benzyl ring and aromatization occurred for the m-methoxybenzyl compound.