2004
DOI: 10.1055/s-2002-19794
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Pyridinium Dichlorobromate: A New Stable Brominating Agent for Aromatic Compounds

Abstract: P y r i d i n i u m D i c h l o r o b r o m a t e , A N e w B r o m i n a t i n g R e a g e n tAbstract: Pyridinium dichlorobromate (PyHBrCl 2 , 1) is a new example of iminium-trihalide complexes. The compound is prepared from pyridine and chlorine in the presence of aqueous hydrogen bromide. The crystalline trihalide is quite stable and acts as a safe source of positive bromine. It shows a remarkable reactivity towards aromatic compounds compared with other bromine complexes. It is also considered as a potent… Show more

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Cited by 14 publications
(11 citation statements)
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“…Instead, post-assembly rotaxane modification was attempted. Electrophilic aromatic bromination using pyridinium dichlorobromate [41] was envisaged as a way to introduce bromine at the 3-and 3 0 -positions of the stilbene of the rotaxane 1 ,based on the chemistry explored by Dumanski et al [42] However,s uch reactions yieldedc omplex mixtures of products. When components were separateda nd analyzed using 1 HNMR spectroscopy,inmost cases there was no evidence of olefinic proton resonances, indicating that addition had occurred across the double bond.…”
Section: Resultsa Nd Discussionmentioning
confidence: 99%
“…Instead, post-assembly rotaxane modification was attempted. Electrophilic aromatic bromination using pyridinium dichlorobromate [41] was envisaged as a way to introduce bromine at the 3-and 3 0 -positions of the stilbene of the rotaxane 1 ,based on the chemistry explored by Dumanski et al [42] However,s uch reactions yieldedc omplex mixtures of products. When components were separateda nd analyzed using 1 HNMR spectroscopy,inmost cases there was no evidence of olefinic proton resonances, indicating that addition had occurred across the double bond.…”
Section: Resultsa Nd Discussionmentioning
confidence: 99%
“…Pyridinium dichlorobromate was prepared by the literature method [15]. Alkaloids used in the reactions were isolated from plant material: (-)-anabasine [(2S)-3-(2-piperidinyl)-pyridine] (10), mp 104-105°C (2 Torr), lit.…”
Section: Methodsmentioning
confidence: 99%
“…Pyridinium dichlorobromate was prepared as described by Muathen. [18] Anisole (3a) was purified by distillation (bp 153-154 • C) before use. 3-Methylacetanilide (7b) was prepared by acetylating m-toluidine.…”
Section: Methodsmentioning
confidence: 99%
“…Instead, they retarded the reaction rate, due to inclusion of both the substrate and the brominating agent. In light of the lack of regiocontrol in this system, the recent account of the use of pyridinium dichlorobromate for aromatic bromination in aqueous methanol [18] prompted us to investigate the effect of employing cyclodextrins with this reagent. As reactants for the study, we chose anisole (3a) and acetanilide (3b), in order to make direct comparisons with the chlorination of those compounds.…”
Section: Introductionmentioning
confidence: 99%