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Synthesis of α-Bromoketones

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1-Arylethanones and related compounds are rapidly brominated in dioxane with the H2O2-HBr aq system, resulting in the replacement of two hydrogen atoms in the methyl group with bromine. The reaction is also accompanied by bromination of the aromatic ring provided that the latter contains electron-donating substituents.
A. O. Terent'ev, S. V. Khodykin, I. B. Krylov, Y. N. Ogibin, G. I. Nikishin, Synthesis, 2006, 1087-1092.


Active methylene compounds can be chemoselectively brominated in high yields using potassium bromide, hydrochloric acid, and hydrogen peroxide at room temperature.
M. Kirihara, S. Ogawa, T. Noguchi, K. Okubo, Y. Monma, I. Shimizu, R. Shimosaki, A. Hatano, Y. Hirai, Synlett, 2006, 2287-2289.


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.


Poly{[4-(hydroxy)(tosyloxy)iodo]styrene} was efficient in the halotosyloxylation reaction of alkynes with iodine or NBS or NCS. The polymer reagent could be regenerated and reused.
J.-M. Chen, X. Huang, Synthesis, 2004, 1557-1558.