Pyridine → Triphenylsulfonium 2-(2-chloroacetoxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate

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Reaction Steps

To a mixture of 148 g (0.30 mole) of triphenylsulfonium 2-hydroxy-1,1,3,3,3-pentafluoropropane-1-sulfonate synthesized in Synthesis Example 1-11, 37.3 g (0.33 mole) of chloroacetyl chloride, and 600 g of acetonitrile, 28.5 g (0.36 mole) of pyridine was added dropwise, followed by stirring at room temperature for 3 hours. The reaction solution was then concentrated and combined with 300 g of 5% dilute hydrochloric acid and 600 g of dichloromethane whereupon the organic layer was separated. The organic layer was washed with 300 g of water, from which dichloromethane was distilled off under vacuum. To the residue was added 600 g of methyl isobutyl ketone. This was washed with 300 g of water, with 300 g of dilute aqueous ammonia, and three times with 300 g of water whereupon methyl isobutyl ketone was distilled off under vacuum. The residue was purified by adding ether for recrystallization, filtered and dried. The target compound was obtained as white crystals (158 g, yield 92%).

Provenance & Evidence