Regioselective Bromination of Anilines in the Presence of Nitrosonium Hydrogensulfate in Concentrated Sulfuric Acid

Gorelik, M. V.; Lomzakova, V. I.; Khamidova, E. A.; Shteiman, V. Ya.; Кузнецова, М. Г.; Andrievsky, A. M.

doi:10.1070/mc1995v005n02abeh000460

Cited by 3 publications

(2 citation statements)

References 5 publications

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“…(E)-1-((4-Bromophenyl)diazenyl)naphthalene-2-ol ( 33 ) [90,91,92]: Assessed loading 11.3 mmol, 90%; Isolated 3.52 g, 86%. 1 H-NMR (400 MHz, CDCl 3 ) δ/ppm: 16.06 (1H, s), 8.56–8.50 (1H, d, J = 8.4 Hz), 7.73 (1H, d, J = 9.5 Hz), 7.60–7.68 (1H, m,), 7.60 (4H, m), 7.56 (1H, ddd, J = 8.3, 7.3, 1.5 Hz), 7.44–7.37 (1H, m), 6.86 (1H, d, J = 9.4 Hz,).…”

Section: Methodsmentioning

confidence: 99%

Exploring Flow Procedures for Diazonium Formation

Baxendale

Baumann

2016

Molecules

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Abstract:The synthesis of diazonium salts is historically an important transformation extensively utilized in dye manufacture. However the highly reactive nature of the diazonium functionality has additionally led to the development of many new reactions including several carbon-carbon bond forming processes. It is therefore highly desirable to determine optimum conditions for the formation of diazonium compounds utilizing the latest processing tools such as flow chemistry to take advantage of the increased safety and continuous manufacturing capabilities. Herein we report a series of flow-based procedures to prepare diazonium salts for subsequent in-situ consumption.

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Section: Methodsmentioning

confidence: 99%

Exploring Flow Procedures for Diazonium Formation

Baxendale

Baumann

2016

Molecules

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“…The reaction of anilines, ortho-and meta-substituted anilines and N,N-dialkyl-anilines in sulfuric acid with bromine and nitrosonium hydrogen sulphate has been resulted in preparation of 4-bromoanilines. The bromination process did not proceed without the presence of the nitrosonium ion [46]. As a result of the reacting anilines and benzyltriphenyl-phosphonium tribromide in condition of dichloromethane and methanol in the presence of sodium bicarbonate at room temperature for several minutes the polybromoanilines were obtained [47].…”

Section: Scheme 29 схема 29mentioning

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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