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

HRID 2199388Notes

Reaction equation

HRID 2199388 reaction equation
[C:1]1([S:7]([CH2:9][Cl:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1.[F:19][C:20]([F:33])([F:32])[S:21]([O:24]S(C(F)(F)F)(=O)=O)(=[O:23])=[O:22]>C(OCC)C>[O-:24][S:21]([C:20]([F:33])([F:32])[F:19])(=[O:23])=[O:22].[Cl:10][CH2:9][S+:7]([C:17]1[CH:16]=[C:15]([CH3:18])[CH:14]=[CH:13][C:12]=1[CH3:11])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7809P-XyleneHCID 67749Trifluoromethanesulfonic anhydrideHCID 81624Chloromethyl phenyl sulfoxide

Product 1

HCID 131735039(Chloromethyl)(2,5-dimethylphenyl)(phenyl) sulfonium triflate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  1. temperaturethe mixture was cooled to a temperature below −60° C
  2. additionwas added slowly
  3. temperaturemaintaining the same temperature

Sources & evidence

ORD record
ord-9c9f8386d285446593bdb7c7a8fd9c2f
Source dataset
uspto-grants-2016_06
Patent number
US09359294B2

Reaction notes

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