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Mesityl bromination

2015-11-16View Original

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I originally wanted to buy m-chloroaniline, but it seems to be quite expensive. Someone suggested that aniline could first be acidified with hydrobromic acid or a salt acid to form an anilinium acid or hydrobromide salt; after filtration, aniline could be extracted from the solid using a solvent. The solid was then dissolved or suspended in a solvent, and bromine was added drop by drop to form the m-bromoanilinium acid or hydrobromide salt, which was subsequently neutralized to yield m-bromoaniline. Ammonia is originally an ortho-para directing group, but once it forms an amonium or ammonium salt, it becomes a meta directing group? Even if it is a meta-directing group, isn’t it easy to introduce bromine at the ortho or para positions? In this way, a mixture of adjacent pairs is formed. So, what is the concentration of m-bromaniline? 90%? 80%? 70%? The content is low, so purification is needed, which increases the costs. Please give some suggestions. I originally wanted to post it in the Chemical Engineering Theory discussion forum. It seems I can’t find this section.
Reply #22018-12-28
My hydrochloride is an ortho-directing group, but it does not react. It’s as if the nitro group is a meta-directing group, but the meta positions of *** are completely deactivated, preventing bromination of the benzene ring
Reply #32020-02-24
***Can’t brominate? What about chlorination?

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