After finding in a previous study that naphthalene and quinoline can react via electrophilic aromatic addition reaction (Ad E Ar), we applied this to anthracene. When anthracene was reacted with bromine in methanol in the presence of NaHCO 3 and pyridine, 9,10-dihydro-9,10-dimethoxyanthracene (2) was obtained in 82% yield in the absence of substitution products or oxidative demethylation products like anthraquinone. The same reaction in ethanol produced 9,10-diethoxy-9,10-dihydroanthracene (9) in much lower yield (45%). In addition, we investigated the reactivity of addition product 2. Treatment of 2 with DDQ in benzene at 65°C for 12h produced 9,10-dimethoxyanthracene (3) in 62% yield, and 2 was rapidly transformed to 9-methoxyanthracene (4) in methanolic NaOH in 10min. Moreover, the acid-catalyzed aromatization of 2 in 1-propanol at 75°C for 10min gave 9-n-propoxyanthracene (8) in 65% yield.