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  • Iodine(III)-mediated umpolung of bromide salts for the ethoxybromination of enamides.

Iodine(III)-mediated umpolung of bromide salts for the ethoxybromination of enamides.

Organic letters (2013-04-02)
Sophie Nocquet-Thibault, Pascal Retailleau, Kevin Cariou, Robert H Dodd
PMID23540374
ABSTRACT

Using (diacetoxyiodo)benzene in conjunction with simple bromide salts in ethanol allows the regioselective ethoxybromination of a wide range of enamides, thus yielding highly versatile α-bromo hemiaminals, which can then be engaged in a broad array of transformations.

MATERIALS
Product Number
Brand
Product Description
449873
Sigma-Aldrich
Lithium bromide, AnhydroBeads™, −10 mesh, ≥99.9% trace metals basis
Pricing and availability is not currently available.
213225
Sigma-Aldrich
Lithium bromide, ReagentPlus®, ≥99%
Pricing and availability is not currently available.
429465
Sigma-Aldrich
Lithium bromide, AnhydroBeads™, −10 mesh, 99.999% trace metals basis
Pricing and availability is not currently available.
229733
Sigma-Aldrich
Lithium bromide, powder and chunks, ≥99.995% trace metals basis
Pricing and availability is not currently available.
411515
Sigma-Aldrich
Lithium bromide solution, 54 wt. % in H2O
Pricing and availability is not currently available.