One Pot Synthesis of New Powerful Building Blocks in 1,8-Naphthalimide Chemistry

This communication reports a reliable one-pot synthetic protocol for preparation on a multigram scale of 3-bromo- and 3,4-dibromo-6-nitro-1,8-naphthalic anhydride from commercially available and economical 1,8-naphthalic anhydride. The synthetic steps used were nitration and selective bromination in sulfuric acid at room temperature. The reaction takes place under mild conditions and is completely controllable depending on the equivalents of the brominating reagent used. Both anhydrides are powerful building blocks in naphthalimide chemistry. In addition, their imides and esters were also synthesized.