Selective bromination of halobenzenes using zeolite catalysts

Wortel, Th. M.; Oudijn, D.; VLEUGEL, C. J.; Roelofsen, D. P.; Bekkum, H. van

doi:10.1016/0021-9517(79)90073-3

Cited by 65 publications

(5 citation statements)

References 8 publications

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“…Wortel et al reported that the bromination of halobenzenes using bromine can be achieved at 25 °C in the presence of cation-exchanged Y-zeolites as catalysts. 306 They reported that the catalyst activity and para/ortho ratio depend upon the type of cation, the extent of cation exchange, the activation temperature, the solvent, and the amount of catalyst used. It was found that in all cases the para/ortho ratio was considerably higher than that with conventional procedures.…”

Section: Bromination Reactions 31 Bromination With Molecular Brominementioning

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 Reactions 31 Bromination With Molecular Brominementioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…Silica has been used as a catalyst for the bromination of various aromatics with NBS , and with polymer-bound tribromide . Initial work on bromination using bromine and zeolites was carried out by van Bekkum et al This work did not lead to particularly high para selectivities, which was attributed to the role of the HBr formed during the reaction. Neutralisation of this acid with bicarbonate did not lead to significant improvements in selectivity.…”

Section: Solid Acidsmentioning

confidence: 99%

Heterogeneous Catalysis in Liquid Phase Transformations of Importance in the Industrial Preparation of Fine Chemicals

and

Macquarrie

1997

Org. Process Res. Dev.

123

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This review focuses on the use of heterogeneous catalysts in the production of fine and speciality chemicals. The major emphasis is on those systems which have been commercialised already and those which are close to commercialisation. These include the use of TS-1 for oxidation reactions including the production of hydroquinone, caprolactam, and alkene oxides, and clay-supported catalysts such as clayzic, which are commercially available for acid-catalysed reactions, in particular Friedel−Crafts reactions. Base catalysis and acid-catalysed halogenation and nitration are also covered.

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“…Moreover, aryl bromides have been used as classical precursors to organolithium and Grignard reagents as well as in benzyne generation and nucleophilic aromatic substitution [10,11]. The most common synthetic method for preparing aryl bromides is electrophilic aromatic bromination, which continues to be an area of focus in synthetic chemistry because aryl bromides are very useful intermediates in the production of drugs, pharmaceuticals, agrochemicals, pigments, photographic materials, and various functional natural products [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37]. This makes the development of regioselective electrophilic aromatic brominations a high priority.…”

Section: Introductionmentioning

confidence: 99%

“…LDH-CO 3 2− -Br 3 − can be used for para -selective monobromination of some aromatic compounds [13]. Zeolites induce high para -selectivity for electrophilic bromination of substrates akin to toluene [14,15,16,17,18,19,20,21,22]. N -bromosuccinimide (NBS)/silica gel is also a good brominating agent for regioselective electrophilic aromatic brominations [23,24].…”

Section: Introductionmentioning

confidence: 99%

Regioselective Electrophilic Aromatic Bromination: Theoretical Analysis and Experimental Verification

Dai

Song

et al. 2014

Molecules

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Electrophilic aromatic bromination is the most common synthetic method used to prepare aryl bromides, which are very useful intermediates in organic synthesis. To understand the experimental results in electrophilic aromatic brominations, ab initio calculations are used here for a tentative analysis of the positional selectivity. The calculated results agree well with the corresponding experimental data, and the reliability of the resulting positional selectivity was verified by the corresponding experimental data.

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Selective bromination of halobenzenes using zeolite catalysts

Cited by 65 publications

References 8 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Heterogeneous Catalysis in Liquid Phase Transformations of Importance in the Industrial Preparation of Fine Chemicals

Regioselective Electrophilic Aromatic Bromination: Theoretical Analysis and Experimental Verification

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