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What is the most efficient method for the preparation of 2,4-dichloronitrobenzene from nitrobenzene and chlorine gas, and what are the optimal reaction conditions (temperature, pressure, solvent, etc.) for this synthesis process?

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The most efficient method for the preparation of 2,4-dichloronitrobenzene from nitrobenzene and chlorine gas is through electrophilic aromatic substitution. In this process, nitrobenzene reacts with chlorine in the presence of a catalyst, such as aluminum chloride  AlCl3  or ferric chloride  FeCl3 , which helps to generate the electrophile  Cl+  and facilitate the reaction.Optimal reaction conditions for this synthesis process are as follows:1. Temperature: The reaction is typically carried out at a temperature between 0C and 5C. Lower temperatures help to minimize the formation of undesired by-products, such as trichloronitrobenzene.2. Pressure: The reaction can be performed under atmospheric pressure.3. Solvent: A non-polar solvent, such as carbon tetrachloride  CCl4  or dichloromethane  CH2Cl2 , is used to dissolve the reactants and catalyst. These solvents are suitable because they do not interfere with the reaction and can dissolve both the nitrobenzene and the catalyst.4. Catalyst: As mentioned earlier, aluminum chloride  AlCl3  or ferric chloride  FeCl3  are commonly used as catalysts for this reaction. The catalyst is typically used in a 1:1 molar ratio with respect to nitrobenzene.5. Reaction time: The reaction is usually complete within a few hours, depending on the specific conditions and the scale of the reaction.6. Workup: After the reaction is complete, the mixture is typically quenched with water to hydrolyze the catalyst and any unreacted chlorine. The organic layer containing the product is then separated, washed with water, and dried over anhydrous sodium sulfate  Na2SO4 . The solvent is then removed under reduced pressure, and the crude product can be purified by recrystallization or column chromatography.By carefully controlling the reaction conditions, it is possible to achieve a high yield of 2,4-dichloronitrobenzene with minimal formation of undesired by-products.

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