Aromatic polymers are excellent in terms of mechanical strength, but they have the drawbacks of difficult material processing and manufacturing. An option to mitigate these issues is to use a thermal crosslinker with aromatic polymers to strengthen and stabilize while avoiding byproducts. This study investigates the rearrangement of the model compound methyl-3-acetoxyn2-bromo propionate (Acetoxy-BrH) via a dioxolenium ion and its subsequent reaction with anisole through electrophilic aromatic substitution. To monitor this reaction, aliquots were collected at regular intervals and analyzed using nuclear magnetic resonance (NMR) spectroscopy. The NMR results confirmed the substitution of the brominated carbon from model onto the para position of the aromatic ring. This reaction serves as an archetype for 1,6-hexanedial-bis(2-bromo-3-acetoxypropanoate) (Acetoxy-BrH-dimer), as the end groups are identical. Since the aromatic ring replaced the bromine on the model, it suggests that the dimer will display similar reactivity. The dimer will be purified by column chromatography; thin-layer chromatography (TLC) will be used to determine the optimal solvent system.