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Oxidation of Alkyl Side Chain

How do you ca...

Question

How do you carry out the following conversion?
Aniline to p-bromoaniline.

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Solution

Aniline is heated with acetic anhydride to form acetanilide. Treatment with bromine/acetic acid gives p-bromoacetanilide. Acid/alkaline hydrolysis gives p-bromoaniline.

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Oxidation of Alkyl Side Chain

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