An Improved Method for the Bromination of Metalated Haloarenes via Lithium, Zinc Transmetalation: A Convenient Synthesis of 1,2-Dibromoarenes

Karsten Menzel,* Ethan L. Fisher, Lisa DiMichele, Doug E. Frantz, Todd D. Nelson, and Michael H. Kress

*Merck Research Laboratories, Department of Process Research, Merck & Co., Inc., 466 Devon Park Drive, Wayne, Pennsylvania 19087, Email: karsten_menzelmerck.com

K. Menzel, E. L. Fisher, L. DiMichele, D. E. Frantz, T. D. Nelson, M. H. Kress, J. Org. Chem., 2006, 71, 2188-2191.

DOI: 10.1021/jo052515k

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Abstract

A standard ortho-lithiation/bromination procedure applied to bromoarenes resulted in poor yields of the corresponding 1,2-dibromoarenes. Transmetalation of the aryllithium intermediates with ZnCl₂, followed by bromination, improved the yields of the synthetically useful 1,2-dibromoarenes dramatically.

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Key Words

Ortho Lithiation, Bromination

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ID: J42-Y2006-700