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Bromination of ketones with H2O2–HBr “on water”

Green chemistry : an international journal and green chemistry resource : GC, 2007-01, Vol.9 (11), p.1212-1218 [Peer Reviewed Journal]

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Title:
Bromination of ketones with H2O2–HBr “on water”
Author: Podgoršek, Ajda ; Stavber, Stojan ; Zupan, Marko ; Iskra, Jernej
Subjects: Alcohol
Is Part Of: Green chemistry : an international journal and green chemistry resource : GC, 2007-01, Vol.9 (11), p.1212-1218
Description: Various 1,3-diketones, [small beta]-ketoesters, cyclic ketones, aryl alkyl and dialkyl ketones were effectively brominated with an aqueous HO-HBr system "on water" at room temperature without the need for a catalyst or organic solvent. The resultant brominated ketones were isolated in yields of 69-97% with high selectivity for monobromination dibromination. Reactivity was manipulated by using more diluted aqueous solutions of HO and HBr and the use of an excess of HBr where necessary. Dilution also increases selectivity of ring bromination [small alpha]-bromination of aryl ketones with an activated phenyl ring. Finally, an aqueous HO-HBr system was used for a tandem oxidation-bromination process and alcohols were transformed into [small alpha]-bromoketones. This simple but effective "on water" bromination of ketones with an aqueous HO-HBr system is characterised by the use of inexpensive reagents, a lower impact on the environment and the absence of organic waste that make it a good alternative to existing bromination methods.
Language: English
Identifier: ISSN: 1463-9262
EISSN: 1463-9270
DOI: 10.1039/b707065a
Source: Alma/SFX Local Collection

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