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Electrophilic aromatic sulfonation

3 real reactions from the literature, on anilines, acetanilides and acyl-deactivated arenes. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. EAS sulfonation: o-toluidine (an aniline) with 1) H2SO4, H2O; 2) Δ gives 4-amino-3-methylbenzenesulfonic acid (the arenesulfonic acid).

  2. EAS sulfonation: acetanilide with HOSO2Cl; (2 equiv.) gives N-acetylsulfanilyl chloride (the arenesulfonic acid).

  3. EAS sulfonation: saccharin (an acyl-deactivated arene) and toluene (an alkylbenzene) with HNO3; H2SO4 gives 2-methylbenzenesulfonic acid (the arenesulfonic acid).

    EAS sulfonationRealOChem worksheet