1, 1, 3, 3-Tetrabromoindane and 1, 1, 2, 3, 3-pentabromoindane were efficiently synthesized by photolytic bromination of indane. Subsequent dehydrobromination of them gave the corresponding tribromo-and tetrabromoindenes, which were easily converted to the corresponding bromoindenones by silver-supported hydrolysis. Thermolysis of 3- bromoindenone gave the benzo [c] fluorenone derivative.