Trifluoromethanesulfonic anhydride → 2-Phenyl-3-methyl-8-trifluoromethanesulfonyloxyquinoline

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Reaction Steps

6.4 ml (38 mmol) of trifluoromethanesulfonic anhydride are added dropwise, at 0° C., to a solution of 4.3 g (18.3 mmol) of 2-phenyl-3-methyl-8-hydroxyquinoline in 50 ml of pyridine. The reaction mixture is then stirred for 16 hours at ambient temperature. After evaporating the pyridine, the residue is taken up in 100 ml of water and 100 ml of ethyl acetate. The aqueous phase is extracted with 2×100 ml of ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum to give 6.6 g of 2-phenyl-3-methyl-8-trifluoromethanesulfonyloxyquinoline in the form of a beige solid; M.p.=85° C. (Yield: 99%)

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