Bromination of 4H-cyclopenta[def] phenanthren-1-amine, -2-amine, -3-amine, or -8-amine with bromine in chloroform took place at the 2-, 1-, 8-, or 9-position, respectively. The second bromine was introduced at the 8-, 3-, 2-, or 3-position. Similar regioselectivity was observed in the system of bromine in acetic acid–48% hydrobromic acid and of hydrobromic acid in dimethyl sulfoxide. The corresponding