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When 9,10-dibromoanthracene was treated with bromine in CCl 4  without a catalyst, 1,2,3,4,9,10-hexabromo-1,2,3,4-tetrahydroanthracene ( 3 ) was obtained in 95% yield in the absence of other stereoisomers or rearomatization products. We investigated the base-induced elimination reaction of hexabromide  3  under various conditions. Pyridine-induced elimination of hexabromide  3  afforded 2,9,10-tribromoanthracene ( 12 ) in 75% yield, and tribromide  12  was transformed to trimethoxy compound  13  and trinitrile  14  by copper-assisted nucleophilic substitution reactions.

Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives