A Multistep Synthesis Incorporating a Green Bromination of an Aromatic Ring.

Electrophilic aromatic substitution is a fundamental topic taught in the undergraduate organic chemistry curriculum. A multistep synthesis that includes a safer and greener method for the bromination of an aromatic ring than traditional bromination methods is described. This experiment is multifaceted and can be used to teach students about protecting groups, multistep synthesis, redox reactions/titrations, electrophilic aromatic substitution, and nucleophilic acyl substitution.