Improved preparation of methyl bis(2,2,2-trifluoroethoxy)-bromophosphonoacetate for the stereoselective synthesis of (E)-α-bromoacrylates

Chem Pharm Bull (Tokyo). 2013;61(1):108-10. doi: 10.1248/cpb.c12-00808. Epub 2012 Oct 19.

Abstract

We have established an efficient method for preparing methyl bis(2,2,2-trifluoroethoxy)bromophosphonoacetate, which we developed for the stereoselective synthesis of (E)-α-bromoacrylates. This improved method enables the reagent to be prepared reproducibly in one step from methyl bis(2,2,2-trifluoroethoxy)phosphonoacetate.

MeSH terms

  • Acrylates / chemical synthesis*
  • Acrylates / chemistry
  • Halogenation
  • Phosphonoacetic Acid / analogs & derivatives*
  • Phosphonoacetic Acid / chemical synthesis*
  • Phosphonoacetic Acid / chemistry
  • Stereoisomerism

Substances

  • Acrylates
  • Phosphonoacetic Acid