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ChemicalBook CAS DataBase List Trimethylsulfoxonium iodide
1774-47-6

Trimethylsulfoxonium iodide synthesis

1synthesis methods
Trimethylsulfoxonium iodide is commonly prepared by a reaction of Dimethyl Sulfoxide with ≈2.5 equiv of Iodomethane. After refluxing for 24 h at 80?°C, the reaction mixture is cooled, and the crude solid product is filtered and washed with acetone to give the trimethylsulfoxonium iodide. Iodomethane has to be handled in a fume hood because of its high volatility and toxicity. Excess MeI is used to ensure the completion of the reaction.
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Yield:1774-47-6 65%

Reaction Conditions:

at 70; for 48 h;

Steps:

Trimethyloxosulfonium iodide (7)

Dimethyl sulfoxide (2 mL, 28.2 mmol) and methyl iodide (1.75 mL, 28.1 mmol) were stirred in a pressure vessel, at 70 °C for 48 hrs. The resulting precipitate was filtered, washing with CHCl3, recrystallised from H2O and dried under reduced pressure to afford clear colourless crystals (4.01 g, 18.2 mmol, 65%);

References:

Ledingham, Edward T.;Merritt, Christopher J.;Sumby, Christopher J.;Taylor, Michelle K.;Greatrex, Ben W. [Synthesis,2017,vol. 49,# 12,p. 2652 - 2662] Location in patent:supporting information

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