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A Novel and Practical Method for the N-Bromomethylation of Imides and Isothiazolone 1,1-Dioxides
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1995
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Asymmetric CatalysisHalogenationEngineeringHeterocyclicOrganic ChemistryPractical MethodPhenyl SulfideChemistryIsothiazolone 1,1-DioxidesN-bromomethyl-isothiazolone 1,1-DioxidesPharmacologyHeterocycle ChemistrySynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringAcetic Acid
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.