Process for preparing organo-sulfonium halides

Details Process for preparing organo-sulfonium halides Process for preparing organo-sulfonium halides

1984-03-01

1988-05-10

Moyer, Donald B.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260544K, C07C14906

Patent

active

047434031

ABSTRACT:
Disclosed is a process for preparing organo-sulfonium halide of the formula ##STR1## wherein X is an halide, R.sub.1, R.sub.2 and R.sub.3 are the same or different and are selected from the group consisting of: alkyl having 1 to 24 carbon atoms, inclusive; allyl having 2 to 24 carbon atoms, inclusive; alkenyl having 2 to 24 carbon atoms, inclusive; alkynyl having 2 to 24 carbon atoms, inclusive; aryl having 6 to 24 carbon atoms, inclusive; and wherein said alkyl, allyl, alkenyl, alkynyl and aryl are optionally substituted with a group that is inert to organo-sulfides comprising: reacting an alcohol, e.g. methanol, with an halide derivative which when reacted with an organo-sulfide forms an organo-sulfonium halide, e.g., thionyl halide, sulfuryl halide and carbonyl halide; and then adding an organo-sulfide, e.g., dimethyl sulfide, to the above reaction mixture with agitation while allowing the gas formed to be eliminated so that the organo-sulfonium halide, e.g., trimethyl sulfonium halide, is formed. This process can take place in the presence of an insert solvent, e.g., methylene chloride.

REFERENCES:
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Kirk-Othmer, Encyclopedia of Chemical Technology, 3rd ed. (1983), vol. 22, pp. 233-235.
March, Jerry, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, (1968), p. 343.
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Christie, J. Joseph et al., J. Org. Chem., vol. 48 (1983), pp. 2531-2534.
Kirk-Othmer, Encyclopedia of Chemical Technology (1955), vol. 13, pp. 440-441.
Matzner, Markus et al., Chemical Reviews, vol. 64 (1964), pp. 645 and 657.
House, Herbert O., Modern Synthetic Reactions, 2nd ed. (1972), W. A. Benjamin, publ. pp. 452-453.

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