Download PDF
Synthesis 1989; 1989(10): 771-773
DOI: 10.1055/s-1989-27391
communication
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of 2-Substituted 3,5-Dibromothiophenes via a Rearrangement Reaction: A New Example of a Base-Catalyzed Halogen Dance Reaction

Fritz Sauter* , Hannes Fröhlich, Wolfram Kalt
  • *Institute of Organic Chemistry, Technical University, Getreidemarkt 9, A-1060 Vienna, Austria
Further Information

Publication History

Publication Date:
02 May 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The reaction of 2,3-dibromothiophene with 1 equivalent of lithium diisopropylamide at -80°C, followed by addition of an electrophile (methyl iodide, methanol, allyl bromide, dimethylformamide, cyclohexanone) gives 2-substituted 3,5-dibromothiophenes selectively and in high yields. The substitution pattern of all products was confirmed by unambiguous assignment of all C-atoms via 13C-NMR spectrometry.

      >