Toluene → Ditolyliodonium Trifluoromethanesulfonate

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Into a 2 liter 3-necked round bottom flask equipped with a mechanical stirrer, thermometer, and inlet was charged with agitation 230.394 g (1076.60 mmol) of potassium iodate, 400 g (4341.13 mmol) of toluene and 360 mL of acetic anhydride. The mixture was cooled to -15° C. Trifluoromethanesulfonic acid (325.751 g, 2170.57 mmol) was added dropwise at a rate such that the temperature remained below 5° C. The addition was complete in 2.5 hours. The mixture was allowed to stir for 4 hours at 0° C. The cooling bath was removed and stirring was continued overnight. The mixture was cooled to 0° C. and 537 mL of water was added at such a rate that the temperature remained below 10° C. Dichloromethane (500 mL) was added and the mixture was stirred 30 minutes and allowed to phase split. The dichloromethane phase was separated. To the aqueous phase was added 500 mL of dichloromethane and the mixture was stirred for 30 minutes and allowed to phase split. The dichloromethane phase was separated. The combined dichloromethane phases were concentrated in vacuo at 40° C. to give a brown liquid. Isopropyl ether (800 mL) was added and the mixture was stirred for one hour. The resulting solid was collected by filtration and washed with 800 mL of isopropyl ether. To the solid was added 460 mL of isopropyl alcohol and the mixture was heated to 82° C. for 30 minutes or until the solid dissolved. The solution was diluted with 460 mL of hexane and the mixture was cooled to 0° C. The resulting solid was collected by filtration and washed with a mixture of 200 mL of hexane and 200 mL of isopropyl alcohol. The solid was heated with 460 mL of isopropyl alcohol at 82° C. for 30 minutes or until a homogeneous solution was obtained. The solution was diluted with 460 mL of hexane and the mixture was cooled to 0° C. The solid was collected by filtration and washed with a mixture of 200 mL of hexane and 200 mL of isopropyl alcohol. The solid was then washed with 300 mL of hexane and allowed to air dry to give a white solid (213.92 grams, 43.5% yield, melting point 110-127).

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