I think you can start by benzenethiol (thiophenol) or starting by aniline, to form diazonium salt at 0-5 (temp) then replace by sulfhydryl SH gp with NaHS or KHS followed by oxidation with nitric, chromium trioxide or other oxidizing agents
Go with thiophenol, then oxidise with oxone in acetone/water/methanol mix.
Hydrolysis of benzenesulfonyl chloride is very efficient and fast method :-)
You can also use chlorosulfonic acid for sulfonation, however, it is used in case of activated benzene derivatives.
If you have the aryl halide, or can do a directed metallation, you can add ArLi or ArMgBr to SO3.
Thiophenols are readily oxidized to the disulfide, by many oxidants including those described. I just am not sure what forcing conditions are needed to further oxidize to oxygenated S-S intermediates and force complete S oxidation. The disulfide is likely to be sterically hindered, and the arene ring is activated for ring substitution. I would expect a mixture of products including those promoted by radical rearrangement and heteroatom scission.
O.K. Nelsen. You mentioned the first step of oxidation.
For a starting material calculate first the change in oxidation number from R-SH to R-SO3H, you can also start by the disulfide.
Calculate the amount of KMnO4 required in acidic condition, and use sulfuric as catalyst.
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