Functionalization of naphthalene: a novel synthetic route to brominated naphthoquinones

2012 ARKIVOC  
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).
doi:10.3998/ark.5550190.0013.718 fatcat:6fmlssmtmreexnfdevv5hkltuy