O-Xylene → (Chloromethyl)(3,4-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. O-Xylene (227 mg, 1.1 eq) was added to the previous solution and the mixture 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 precipitated triflate salt was isolated by filtration and washed with diethyl ether at 0° C. (50 mL). 0.602 g (75%) of the desired product was obtained as a oily solid. 1H NMR (CDCl3, 400 MHz): δ 7.93 (2H, d, J=7.9 Hz), 7.74-7.65 (5H, m), 7.44 (1H, d, J=8.1 Hz), 5.86 (2H, s), 2.35 (6H, s). 13C NMR (CDCl3, 100 MHz): δ 146.0, 141.3, 135.1, 132.0, 132.6, 131.6, 131.4, 130.9, 128.6, 122.5, 121.5, 118.3, 117.7, 52.3, 20.0, 19.7. FT-IR (NaCl): 3023, 2956, 1483, 1448, 1226, 1027 cm−1.

Provenance & Evidence