Regioselective and High-Yielding Bromination of Phenols and Anilins Using N-Bromosaccharin and Amberlyst-15

Baharfar, Robabeh; Alinezhad, Heshmatollah; Azimi, Saeid; Salehian, Fatemeh

doi:10.4067/s0717-97072011000400008

Cited by 9 publications

(4 citation statements)

References 17 publications

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“…Again, a regioselective and facile bromination of anilines and phenols using NBSac in the presence of a catalytic amount of Amberlyst-15 was reported by Baharfar et al, which led to an enhanced reaction rate and yielded brominated products in good to excellent yields and a short reaction time . Sanchez and Fumarola reported an efficient method for benzylic and carbonylic bromination using NBSac under mild conditions .…”

Section: Bromination Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Bromination Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…41 This procedure found to be effective over other due its environmental compatibility, greater selectivity, reusability, nontoxicity, ease of isolation, operational simplicity and noncorrosiveness, whereas Baharfar and coworkers evaluated the bromination of anilines and phenols using N-bromosaccharin in catalytic amount of Amberlyst-15 as catalyst (Scheme 27b). 42 This protocol was found to be efficient due to mild reaction conditions, high regioselectivity, rapid conversion, good to excellent yields, and reusability of the catalyst.…”

Section: N-tert-butyloxycarbonyl (N-boc) Protectionmentioning

confidence: 99%

Artificial sugar saccharin and its derivatives: role as a catalyst

Kaur

Srivastava

2020

RSC Adv.

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“…The experiments carried out by using NBS in bromination of aromatic amines (scheme 19) at room temperature in carbon tetrachloride with catalytic action of silica gel have been resulted by the production of parabromo derivatives and ortho-bromo derivatives in a case of para-position substituent [28]. Scheme 19 Схема 19 It has been reported about bromination of aromatic amines by using N-bromosaccharin (NBSac) in the catalytic amount of Amberlyst-15 (scheme 20) [29] and directed bromination of anilines with NBSac, by use of tungstophosphoric acid as a heterogeneous recyclable catalyst, under solventfree conditions [30,31].…”

Section: Scheme 16 схема 16mentioning

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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Regioselective and High-Yielding Bromination of Phenols and Anilins Using N-Bromosaccharin and Amberlyst-15

Abstract: A regioselective and facile conversion method for bromination of anilines and phenols using N-bromosaccharine in the presence of a catalytic amount of Amberlyst-15 lead to enhancement of the reaction rate and yielded brominated products in good to excellent yields and short reaction times.

Cited by 9 publications

References 17 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Artificial sugar saccharin and its derivatives: role as a catalyst

Bromination of Aromatic Amines

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