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Synthesis of α-bromocarboxylic acids and derivatives

Name Reactions

Hell-Volhard-Zelinsky Reaction

Recent Literature

A highly efficient general strategy for the synthesis of 2-amino acids by homologation of α-amino acids, involving the Reformatsky reaction with a Mannich-type imminium electrophile is reported.
R. Moumne, S. Lavielle, P. Karoyan, J. Org. Chem., 2006, 71, 3332-3334.

Reliable and Versatile Synthesis of 2-Aryl-Substituted Cinnamic Acid Esters
A. Ianni, S. R. Waldvogel, Synthesis, 2006, 2103-2112.

1,3-keto esters and 1,3-diketones have been effectively and regioselectively α-monobrominated using bromodimethylsulfonium bromide as reagent.
A. T. Khan, M. A. Ali, P. Goswami, L. H. Choudhury, J. Org. Chem., 2006, 71, 8961-8963.

A mild and rapid formal electrophilic α-azidation of 1,3-dicarbonyl compounds using commercially available Bu4NN3 as the azide source is mediated by (diacetoxyiodo)benzene. The reaction conditions are Bäcklund to the ones employed in analogous halogenations with Et4NX (X = Cl, Br, I).
M. J. Galligan, R. Akula, H. Ibrahim, Org. Lett., 2014, 16, 600-603.


Treatment of widely available isocyanates with monohalolithium and dihalolithium carbenoids provides α-halo- and α,α-dihaloacetamide derivatives. While monohalolithium carbenoids can be prepared by a smooth lithium-halogen exchange, the preparation of the corresponding dihalo compounds proved to be highly dependent on the base used to realize the deprotonation, with lithium 2,2,6,6-tetramethylpiperidine emerging as optimal.
V. Pace, L. Castoldi, A. D. Mamuye, W. Holzer, Synthesis, 2014, 46, 2897-2909.