Categories: C-Br Bond Formation >
Synthesis of α-Bromoketones
Recent Literature
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.
