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Related Concept Videos

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Reactions at the Benzylic Position: Halogenation01:11

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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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Radical Substitution: Allylic Bromination01:27

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Halogenation of Alkenes02:46

Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
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Indium chloride catalysed benzyl bromination using continuous flow technology.

Hajeeth Thankappan1, Conor Burke1, Brian Glennon1

  • 1APC Ltd, Cherrywood Business Park, Loughlinstown, Dublin, Ireland D18 DH50. hajeeth.thankappan@approcess.com.

Organic & Biomolecular Chemistry
|December 19, 2022
PubMed
Summary
This summary is machine-generated.

A new water-tolerant indium chloride catalyst enables efficient green benzyl bromination. This catalyst shows high activity and improved selectivity in continuous flow reactions for various toluene derivatives.

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Area of Science:

  • Green Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Benzyl bromination is a key reaction in organic synthesis.
  • Traditional methods often involve harsh conditions or toxic reagents.
  • Development of sustainable catalytic systems is crucial.

Purpose of the Study:

  • To develop a water-tolerant, green catalyst for benzyl bromination.
  • To evaluate the catalyst's performance in continuous flow.

Main Methods:

  • Utilized indium chloride as a water-tolerant green catalyst.
  • Performed benzyl bromination reactions with various toluene derivatives.
  • Operated the catalytic system under continuous flow conditions.

Main Results:

  • Indium chloride demonstrated high catalytic activity for benzyl bromination.
  • Achieved good product yields ranging from 59-77%.
  • Observed enhanced selectivity under continuous flow compared to batch processes.

Conclusions:

  • Indium chloride is an effective and green catalyst for benzyl bromination.
  • Continuous flow operation improves selectivity and efficiency.
  • This method offers a sustainable alternative for industrial applications.