1,2,3,4-Tetramethylbenzene → (Fluoromethyl)(2,3,4,5-tetramethylphenyl)(p-tolyl)sulfonium triflate

Participants

Reaction Steps

1-((Fluoromethyl)sulfinyl)-4-methylbenzene (3 g, 17.42 mmol) of example 5 was dissolved in dry diethyl ether (100 ml) under nitrogen atmosphere. 1,2,3,4-Tetramethylbenzene (2.60 mL, 1.0 eq) was added to the previous solution and then the mixture was cooled to a temperature below −10° C. Trifluoromethanesulfonic anhydride (2.93 mL, 1 eq) was added slowly maintaining the same temperature. The mixture was stirred at the same temperature, until the reaction was complete. A pink suspension was formed and after 3 hours, turned into a light grey suspension. The precipitate triflate salt was isolated by filtration, washed with diethyl ether at 0° C. and dried under vacuum at a temperature below 30° C. 5.68 g (79.44%) of the desired product was obtained as a white solid.

Provenance & Evidence