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Synlett 1995; 1995(5): 423-424
DOI: 10.1055/s-1995-4994
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A Novel and Practical Method for the N-Bromomethylation of Imides and Isothiazolone 1,1-Dioxides

John J. Court, Thomas A. Lessen, Dennis J. Hlasta*
  • *Department of Medicinal Chemistry, Sterling Winthrop Pharmaceuticals Research Division, Sterling Winthrop Inc., Collegeville, Pennsylvania 19426, U.S.A.
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Publication Date:
31 December 2000 (online)

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An efficient two-step procedure affords bromomethyl phenyl sulfide, N-bromomethyl-imides, and N-bromomethyl-isothiazolone 1,1-dioxides in high yields. S- or N-Alkylation of the substrate 2 with chloromethyl pivalate (POMCl) gives the intermediate pivaloylmethyl derivatives 3 which on treatment with 5% HBr in acetic acid yields the bromomethyl derivatives 4.

Bromomethylation - Imide - Benzisothiazolone - Isothiazolone - Thiophenol