Hydrogen Peroxide → 5-Tert-butyl-1-methanesulphinyl-2-methoxy-3-nitro-benzene

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Reaction Steps

At ambient temperature 1.1 ml of a 35% aqueous hydrogen peroxide solution are added to a solution of 500 mg 5-tert-butyl-2-methoxy-1-methylsulphanyl-3-nitro-benzene (may be obtained starting from 5-tert-butyl-2-methoxy-3-nitro-aniline analogously to the method described in Syn. Commun. 1984, 14, 215-8 or in Syn. Commun. 2001, 31, 1857-62) in 15 ml of 1,1,1,3,3,3-hexafluoroisopropanol. The solution is stirred for 5 h at ambient temperature and then quenched with 10% aqueous Na2S2O3 solution. The resulting mixture is extracted with ethyl acetate, and the combined extracts are washed with saturated aqueous NaHCO3 solution and saturated aqueous saline solution. The organic phase is dried (Na2SO4) and the solvent is distilled off. The residue is chromatographed on silica gel with petroleum ether/ethyl acetate (20:1) as eluant.

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