DOI: 10.1039/A803388I
(Paper)
Reference Section for: J. Chem. Res. (S), 1998, 786-787
An Improved Method for the Preparation of 1-Methyl-2-formyl-5-bromopyrrole
(Note: The full text of this document is currently only available in the PDF Version )
Roderick Hai-Ying He and Xi-Kui Jiang
Abstract
1-Methyl-2-formyl-5-bromopyrrole 1 was prepared in 48% total yield by initial bromination of the intermediate 1-methyl-2-(5,5-dimethyl-1,3-dioxan-2-yl)pyrrole 5 with N-bromosuccinimide to give the intermediate 1-methyl-2-(5,5-dimethyl-1,3-dioxan-2-yl)-5-bromopyrrole 6, which was finally hydrolyzed to the product 1.
References
- (a) X. K. Jiang, Acc. Chem. Res., 1997, 30, 283 CrossRef CAS; (b) X. K. Jiang, G. Z. Ji and D. Z. R. Wang, J. Phys. Org. Chem., 1995, 8, 143 CAS; (c) X. K. Jiang, G. Z. Ji, D. Z. R. Wang and J. R. Y. Xie, J. Phys. Org. Chem., 1995, 8, 781 CAS.
- R. H. Y. He and X. K. Jiang, J. Chem. Res., 1998, submitted Search PubMed.
- P. B. De La Mare and J. H. Ridd, Aromatic Substitution, Butterworths, London, 1959, ch. 8 Search PubMed.
- H. J. Anderson and S. F. Lee, Can. J. Chem., 1965, 43, 409 CAS.
- P. T. Kaye, R. Macrae, G. D. Meakins and C. H. Patterson, J. Chem. Soc., Perkin Trans. 2, 1980, 1631 RSC.
- (a) W. C. Anthony, J. Org. Chem., 1960, 25, 2049 CrossRef CAS; (b) H. M. Gilow and D. E. Burton, J. Org. Chem., 1981, 46, 2221 CrossRef CAS.
- A. H. Jackson, ‘Pyrroles’, in Comprehensive Organic Chemistry, ed. P. G. Sammes, Pergamon Press, London, 1979, vol. 4, p. 290 Search PubMed.
- R. M. Silverstein, E. E. Ryskiewicz, C. Willard and R. C. Koehler, J. Org. Chem., 1955, 20, 668 CrossRef CAS.
- (a) C. E. Loader, G. H. Barnett and H. J. Anderson, Can. J. Chem., 1982, 60, 383 CAS; (b) C. E. Loader and H. J. Anderson, Synthesis, 1978, 295 CrossRef CAS.