P-Xylene → (Chloromethyl)(2,5-dimethylphenyl)(phenyl) sulfonium triflate

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Reaction Steps

Chloromethyl phenyl sulfoxide (300 mg, 1.94 mmol) of example 21 was dissolved in dry diethyl ether (7.5 mL) under an argon atmosphere. p-Xylene (227 mg, 1.1 eq) was added to the previous solution and the mixture was cooled to a temperature below −60° C. After stabilizing the temperature, trifluoromethanesulfonic anhydride (0.326 mL, 1 eq) was added slowly maintaining the same temperature. The mixture was stirred until the reaction was complete. The precipitate triflate salt formed was isolated by filtration and washed with cold diethyl ether at 0° C. 602 mg (75%) of the desired product was obtained as a oily solid after heating at room temperature. δ 7.91 (2H, d, J=7.9 Hz), 7.85 (1H, s), 7.73-7.64 (3H, m), 7.44 (1H, d, J=7.8 Hz), 7.33 (1H, d, J=7.9 Hz), 5.97 (2H, s), 2.52 (3H, s), 2.44 (3H, s). 13C NMR (CDCl3, 100 MHz): δ 140.3, 138.6, 136.1, 135.1, 132.7, 131.5, 131.0, 129.3, 122.2, 121.8, 120.3, 118.7, 51.6, 20.7, 19.3. FT-IR (NaCl): 3025, 2956, 1494, 1448, 1251, 1168, 1029 cm−1.

Provenance & Evidence