Elsevier

Tetrahedron Letters

Volume 41, Issue 13, 27 March 2000, Pages 2083-2085
Tetrahedron Letters

Mild and regioselective oxidative bromination of anilines using potassium bromide and sodium perborate

https://doi.org/10.1016/S0040-4039(00)00119-2Get rights and content

Abstract

The selective monobromination of various deactivated anilines using potassium bromide and sodium perborate as oxidant has been achieved. The use of ammonium molybdate as catalyst accelerates the rate of reaction but is not essential to obtain good yields and high selectivities.

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Acknowledgements

The authors thank Dr. Tao He (Novartis) for his expertise in mass spectroscopy.

References (5)

  • March, J. Advanced Organic Chemistry; 3rd ed., Wiley: New York, 1985; pp....
  • (a) Berthelot, J.; Guette, C.; Essayegh, M.; Desbene, P. L.; Basselier, J. J. Synth. Com. 1986, 16, 1641–1645; (b)...
There are more references available in the full text version of this article.

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