Overall Score4
- Generality
- Reagent Availability
- Experimental User Friendliness
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General Characteristics
Aromatic nitriles can be synthesized from the corresponding aryl halides using copper(I) cyanide. The reaction tends to require high temperature conditions but is straightforward operationally.
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General References
- Rosenmund, K. W.; Struck, E. Ber. Dtsch. Chem. Ges. 1919, 52, 1749. doi:10.1002/cber.19190520840
- Pongratz, A. Monatsh. Chem.1927, 48, 585. doi:10.1007/BF01518076
- von Braun, J.; Manz, G. Liebigs Ann. Chem.1931, 488, 111. doi:10.1002/jlac.19314880107
- Koelsch, C. F.; Whitney, A. G. J. Org .Chem.1941, 6, 795. doi:10.1021/jo01206a002
- Callen, J. E.; Dornfeld, C. A.; Coleman, G. H. Org. Synth.1948, 28, 34. [PDF]
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Reaction Mechanism
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Examples
The newer modified method uses a substoichiometric amount of copper.[1]
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Experimental Tips
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References
[1] Zanon, J.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 2890. DOI: 10.1021/ja0299708
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Related Reactions
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Related Books
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External Links
- Rosenmund-von Braun Reaction (organic-chemistry.org)
- Rosenmund-von Braun Reaction – Wikipedia