The bromination of 8,16-dimethyl[2.2]metacyclophan-1-ene with bromine in carbon tetrachloride solution at room temperature for 10 min afforded trans-2,4,7,9-tetrabromo-10b,10c-dimethyl-10b,10c-dihydropyrene in 79% yield; similar reaction of 5,13-dichloro-8,16-dimethyl[2.2]metacyclophan-1-ene at room temperature for 2 h gave trans-2,7-dichloro-4,9-dibromo-10b,10c-dimethyl-10b,10c-dihydropyrene in 25% yield.