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

Participants

Reaction Steps

1-((chloromethyl)sulfinyl)-4-methylbenzene (500 mg, 2.65 mmol) of example 29 was dissolved in dry diethyl ether (5 mL) under an argon atmosphere. 1,2,3,4-Tetramethylbenzene (0.40 mL, 1 eq) was slowly added to the previous solution and then the mixture was cooled to a temperature between 5° C. and 0° C. After stabilizing the temperature, trifluoromethanesulfonic anhydride (0.45 mL, 1 eq) was added maintaining the same temperature. The mixture was stirred until the reaction was complete. The precipitated triflate salt was isolated by filtration and washed with diethyl ether (5 mL) at 0° C. 1.12 g (89.74%) of the desired product was obtained as a white solid. Mp=28-30° C.

Provenance & Evidence