O-Xylene → (Chloromethyl)(3,4-dimethylphenyl)(phenyl) sulfonium triflate

HRID 2199387Notes

Reaction equation

HRID 2199387 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][CH:15]=[CH:16][C:17]=1[CH3:18].[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:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[C:12]([CH3:11])[CH:13]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 67749Trifluoromethanesulfonic anhydrideHCID 81624Chloromethyl phenyl sulfoxide

Product 1

HCID 131735037(Chloromethyl)(3,4-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. 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.

Workup

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

Sources & evidence

ORD record
ord-c128585acc1e404ab069959eee3a3352
Source dataset
uspto-grants-2016_06
Patent number
US09359294B2

Reaction notes

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