S(Cl)(Cl)=O.[CH3:5][S:6](O)(=[O:8])=[O:7].[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)([O-:12])=[O:11].FC(F)(F)S(O)(=O)=O>C(OCC)(=O)C.O>[CH3:5][S:6]([C:17]1[CH:18]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=[CH:15][C:16]=1[CH3:19])(=[O:8])=[O:7]
Under a nitrogen atmosphere, thionylchloride (4 ml, 58 mmol) and methanesulphonic acid (9 mL, 146 mmol) were refluxed for 90 min. 4-Nitrotoluene (4 g, 29 mmol) and triflouromethanesulphonic acid (200 uL, 3 mmol) were added and the mixture was allowed to stand for 48 hours at 120° C. The mixture was cooled to 0° C. and water (50 mL) was carefully added, followed by addition of ethyl acetate (150 mL). The organic phase was separated and extracted with a saturated solution of sodium hydrogencarbonate (2×50 mL) and water (2×50 mL). The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (heptane/ethylacetate, 1:1) to give 0.75 g of 2-methylsulfonyl-1-methyl-4-nitrobenzene.
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