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  Home > JCE Print > Journal of Chemical Education > Issues > 1997  > July  >
In the Laboratory
The Microscale Laboratory
Synthesis of 4-Nitro-1-Pentynylbenzene: An Example of Transitional Metal-Mediated Cross-Coupling
Ronald G. Brisbois, William G. Batterman, and Scott R. Kragerud
Cover
July 1997
Vol. 74 No. 7
p. 832
Abstract
A procedure for the preparation and purification of 4-nitro-1-pentynylbenzene is reported for use as an introductory organic laboratory exercise. Synthesis of the target compound exemplifies contemporary Pd-mediated cross-coupling methodologies. In this regard, several fundamental mechanistic aspects of catalytic organometallic chemistry are illustrated, including oxidative addition, transmetallation, and reductive elimination. Purification of the target compound via flash column chromatography exposes students to a central technique of modern synthetic methodology. Spectroscopic characterization of the target compound reinforces fundamental skills in 1H NMR, 13C NMR, and IR analysis and interpretation.
More Information
*  Citation
 Brisbois, Ronald G. ; Batterman, William G.; Kragerud, Scott R. J. Chem. Educ. 1997 74 832.
*  Keywords
 Organic Chemistry, Laboratory Instruction, Microscale, Organic Synthesis, Organometallics, Palladium
*  History
 Created:
Last Updated:		 July 28, 1999
June 23, 2005
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