An efficient procedure is described for synthesis of 2,5,8-tribromonaphthoquinone (12) from naphthalene in four reaction steps. Silver-promoted solvolysis of hexabromide 3 produces the specific diastereostereoisomer 10. Dehydrobromination of 10 using sodium methoxide gives tribromodihydronaphthalene-1,4-diol 11 in high yield. PCC oxidation of either 10 or 11 results in the formation of 2,5,8-tribromonaphthalene-1,4-dione (12).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.