An effective and regioselective bromination of 1,4,5,8-naphthalenetetracarboxylic dianhydride using tribromoisocyanuric acid

A highly efficient and cost-effective reagent for the bromination of 1,4,5,8-naphthalenetetracarboxylic dianhydride under mild reaction conditions is reported. Bromination of 1,4,5,8-naphthalenetetracarboxylic dianhydride using tribromoisocyanuric acid (TBCA) in concentrated H2SO4 is very effective and regioselective. 1,4,5,8-Naphthalenetetracarboxylic dianhydride was brominated smoothly under optimized reaction conditions to give mono-, di- and tetra-brominated products in good to excellent yields using TBCA. As a proof of principle, the potential of this bromination methodology is demonstrated by converting brominated naphthalenetetracarboxylic dianhydrides into N-imide and core functionalized 1,4,5,8-napthalenetetracarboxylic diimides by treating with n-butylamine to yield corresponding mono-, di- and tetra-(n-butylamino)-naphthalene diimides in good yields in one-step reactions.