Efficient and Regioselective Bromination of Aromatic Compounds with Ethylenebis(N-methylimidazolium) Ditribromide (EBMIDTB)

Hosseinzadeh, Rahman; Tajbakhsh, Mahmood; Mohadjerani, Maryam; Lasemi, Zahra

doi:10.1080/00397910903019975

Cited by 26 publications

(13 citation statements)

References 33 publications

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“…Indeed the 4,5-dihalogenated adduct can be obtained in synthetically useful yields. [16][17][18] In fact all three positions in N-methylimidazole can be halogenated which is not surprising given the fact the calculations suggest that the three possible arenium ions have similar standard free energies. [19][20][21] Finally, a 1 : 1 mixture of the 4-and 5-brominated products has been reported for N-benzylimidazole, which is in line with the predictions.…”

Section: Introductionmentioning

confidence: 83%

Fast and Accurate Prediction of the Regioselectivity of Electrophilic Aromatic Substitution Reactions

Jimmy¹,

Jensen²,

Monika³

et al. 2017

Preprint

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While computational prediction of chemical reactivity is possible it usually requires expert knowledge and there are relatively few computational tools that can be used by a bench chemist to help guide synthesis. The RegioSQM method for predicting the regioselectivity of electrophilic aromatic substitution reactions of heteroaromatic systems is presented in this paper. RegioSQM protonates all aromatic C-H carbon atoms and identifies those with the lowest free energies in chloroform using the PM3 semiempirical method as the most nucleophilic center. These positions are found to correlate qualitatively with the regiochemical outcome in a retrospective analysis of 96% of more than 525 literature examples of electrophilic aromatic halogenation reactions. The method is automated and requires only a SMILES string of the molecule of interest, which can easily be generated using chemical drawing programs such as ChemDraw. The computational cost is 1-10 minutes per molecule depending on size, using relatively modest computational resources and the method is freely available via a web server at regiosqm.org. RegioSQM should therefore be of practical use in the planning of organic synthesis.

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Section: Introductionmentioning

confidence: 83%

Fast and Accurate Prediction of the Regioselectivity of Electrophilic Aromatic Substitution Reactions

Jimmy¹,

Jensen²,

Monika³

et al. 2017

Preprint

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“…The regioselectivity witnessed in these reactions matches to that predictable for an electrophilic bromination path modulated by steric effects. We observed that oxine (8) and sulfanilamide (9) (Table no. 6, entries 12 to 16) in outstanding end product yields at 25℃ upon simple admixing with aq.…”

Section: Iv) Stirringmentioning

confidence: 88%

A Direct and Simplistic Bromination of Commercially Important Organic Compounds in Aqueous Media by Eco-friendly AlBr3-Br2 Reagent System

Sharma¹,

Agarwal²

2015

ujc

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“…It has been reported about a regioselective method of bromination of the aniline derivatives at room temperature in dichloromethane with ethylenebis(Nmethylimidazolium) ditribromide and the possibility of using this isolated reagent several times [59].…”

Section: Scheme 34 схема 34mentioning

confidence: 99%

Bromination of Aromatic Amines

Mustafayeva

Kakhramanov

2019

IVKKT

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It is known that the antipyrenes, biological active substances (antitumor, antibacterial, antifungal, antiviral), pharmacological preparations on the basis of bromine-containing aromatic compounds are widely used in the industry. Considering this and increased demand for these substances the purpose of this work was to summarize and systematize the accumulated knowledge in this area. The article presents methods and reagent systems used in the bromination of aromatic amines. There have been described the bromination of aromatic amines with hydrogen bromide, sodium bromide, potassium bromide, ammonium bromide, copper (II) bromide, N-bromosuccinimide, N-bromosaccharin, polymer-supported halogenation agents, and difference of these methods from the point of view of the used oxidizer, the medium and the solvent, the catalyst, the regioselectivity, the quantity of bromine atoms in the obtained product. The influence of solvents, catalysts, the nature (electron-donor or electron-acceptor) and position (ortho-, meta-, para-) of the substituents in the aromatic ring, reaction conditions, molar ratio of the reagents, reaction temperature and carrying out time of bromination reaction of aromatic amines has been shown. The bromination reactions courses of aromatic amines in different solvents, in solvent free conditions, in solid states has been described. The bromination of aromatic amines under thermal, microwave, ultraviolet radiation conditions has been studied. In the paper the regioselective monobromination and also obtaining of di-, tri- bromo derivatives of aromatic amines has been shown. Taking into account today's priority to environmentally safe methods of bromination of aromatic amines they have been also mentioned. Given the above, in our opinion, the information presented in this article will help to optimize the production of bromo derivatives of aromatic amines used in industry, technics and technology.

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Efficient and Regioselective Bromination of Aromatic Compounds with Ethylenebis(N-methylimidazolium) Ditribromide (EBMIDTB)

Cited by 26 publications

References 33 publications

Fast and Accurate Prediction of the Regioselectivity of Electrophilic Aromatic Substitution Reactions

Fast and Accurate Prediction of the Regioselectivity of Electrophilic Aromatic Substitution Reactions

A Direct and Simplistic Bromination of Commercially Important Organic Compounds in Aqueous Media by Eco-friendly AlBr<sub>3</sub>-Br<sub>2</sub> Reagent System

Bromination of Aromatic Amines

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