O-Xylene → (3,4-Dimethylphenyl)(fluoromethyl)(p-tolyl)sulfonium tetrafluoroborate

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Reaction Steps

1-((Fluoromethyl)sulfinyl)-4-methylbenzene (576 mg, 3.34 mmol) of example 5 was dissolved in dry diethyl ether (15 mL) under argon atmosphere. O-Xylene (0.445 mL, 1.10 eq) was added to the previous solution. The mixture was cooled to a temperature below −50° C. After stabilizing the temperature below −50° C., trifluoromethanesulfonic anhydride (0.562 mL, 1 eq) was added slowly maintaining the same temperature. The mixture was stirred, until the reaction was complete. HBF4 in diethyl ether solution (54%, 0.921 mL, 2 eq) was added. The resulting suspension was stirred for 30 minutes. The precipitate tetrafluoroborate salt was isolated by filtration and washed with diethyl ether at 0° C. The desired product was obtained as an oily solid (1.42 g).

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