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We have developed a new one pot synthesis of triphenylsulfonium salts using inexpensive starting materials which are available in bulk. ***** SEE ORIGINAL FOR MATHEMATICAL EQUATIONS IN DOCUMENT *****
English (United States)
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Synthesis of Triarylsulfonium Salts
We have developed a new one pot synthesis of triphenylsulfonium salts using
inexpensive starting materials which are available in bulk. ***** SEE ORIGINAL
FOR MATHEMATICAL EQUATIONS IN DOCUMENT *****
This process can be used to make simple sulfonium salts (e.g. Ph3S+ Br-, a
useful reagent for the synthesis of sulfonium salts by metathesis and heterolysis
reactions) and complex sulfonium salts (Ar3S+ BF4) in one pot. The starting
materials for this process (aryl halides, magnesium and thionyl halides) are
materials available in bulk quantities commercially.
The Grignard reagent (1 equivalent, prepared from stoichiometric amounts
bromobenzene and Mg in ether), was heated under vacuum to remove solvent.
To the residue was added benzene or toluene followed by n-Heptane. The
solution was heated to about 80oC and thionyl chloride (1/6 equivalent) was
added. Heating was continued for three hours. The cooled reaction mixture was
quenched with 1.5 equivalents of 25% aqueous HBr per equivalent of Grignard
reagent (exotherm!). Two layers separated and the organic layer was extracted
with 5% aqueous HBr. The combined aqueous solutions were extracted with
dichloromethane. The combined organic extracts were dried over MgSO4,
filtered and evaporated. The residue was dissolved in dichloromethane and the
product precipitated by adding ether. The material compared with an authentic
sample by m.p. and IR spectroscopy.