Synthetic efforts toward poly(arylmethyl sulfone) dendrimers are described. A molecule designed to function as a protected AB2 monomer, phenyl 3,5-bis(chloromethyl)-benzenesulfonate was synthesized in four steps from dimethyl 5-sulfoisophthalate in 59% overall yield. This monomer was coupled to sodium benzenesulfinate to give the generation 1 monodendron, phenyl 3,5-bis(phenylsulfonylmethyl)benzene-sulfonate. However, deprotection of the generation 1 monodendron by literature methods of reduction and hydrolysis were not successful.