Rosenmund–von Braun reaction

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The Rosenmund–von Braun synthesis is an organic reaction in which an aryl halide reacts with cuprous cyanide to an aryl nitrile.[1][2][3]

Rosenmund–von Braun synthesis

The reaction was named after Karl Wilhelm Rosenmund who together with his Ph.D. student Erich Struck discovered in 1914 that aryl halide reacts with alcohol water solution of potassium cyanide and catalytic amounts of cuprous cyanide at 200°C. The reaction yields the carboxylic acid, not the nitrile, but Rosenmund speculated that the intermediate should be the nitrile.[1] Independently Alfred Pongratz[4] and Julius von Braun[2] improved the reaction by changing the reaction conditions to higher temperatures and used no solvent for the reaction. Further improvement of the reaction was done in the following years,[5] for example the use of ionic liquids as solvent for the reaction.[6]

Other example

References[edit]

  1. ^ a b Karl Wilhelm Rosenmund, Erich Struck (1919). "Das am Ringkohlenstoff gebundene Halogen und sein Ersatz durch andere Substituenten. I. Mitteilung: Ersatz des Halogens durch die Carboxylgruppe". Chemische Berichte 52: 1749. doi:10.1002/cber.19190520840. 
  2. ^ a b Julius von Braun, Gottfried Manz (1931). "Fluoranthen und seine Derivate. III. Mitteilung". Liebigs Annalen der Chemie 488: 111–126. doi:10.1002/jlac.19314880107. 
  3. ^ For an example see: Organic Syntheses, Coll. Vol. 3, p.212 (1955); Vol. 28, p.34 (1948). http://www.orgsynth.org/orgsyn/pdfs/CV3P0212.pdf
  4. ^ Alfred Pongratz (1927). "Untersuchungen über Perylen und seine Derivate". Monatshefte für Chemie 48 (7): 585–591. doi:10.1007/BF01518076. 
  5. ^ C. F. Koelsch, A. G. Whitney (1941). "The Rosenmund–von Braun nitrile synthesis". Journal of Organic Chemistry 6 (6): 795–803. doi:10.1021/jo01206a002. 
  6. ^ Jeff Xin Wu, Brandon Beck and Rex X. Ren (2002). "Catalytic Rosenmund–von Braun reaction in halide-based ionic liquids". Tetrahedron Letters 43 (3): 387–389. doi:10.1016/S0040-4039(01)02168-2.