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4,5-Dibromoisatin synthesis

  1. Dec 4, 2004 #1


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    Hello, I wonder if this chemical can be synthesized. I have devised a retrosynthetic analysis route, but not sure if this may work or not.

    I have considered that 1,2-dibromobenzene may be nitrated (or 1,2-dibromo-4-nitrobenzene may be purchased instead) to give nitro derivative, which will be reduced to the amine, then tosylated (protected) and reacted with 1-chloroethylene glycol via Friedel-Crafts alkylation (I am really not sure about this step to work). Deprotection of tosyl group will give the amine compound, or simply oxidizing this with acidic permanganate solution to give the ketoacid, and then deprotecting (which sounds better, but not present in the attachment). The acid may be activated with, say, [tex]\displaystyle Ph_3P+CBr_4[/itex], and reacted with the amine to give the cyclic amide, which we call as isatin.

    In addition, I wonder if the other dibromo isomers may be synthesized, I put their formulae in the attachment. I think they are not easily synthesized, and actually 4,5-dibromo derivative is much more suitable to my needs.

    Thank you for your interest.

    P.S. I have seen that there are better ways like Sandmeyer's isonitroacetanilide isatin synthesis and Sandmeyer's Diphenylurea isatin synthesis. So you may compare my route with them, or just answer the question sign in my attachment about how to achieve this step.

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    Last edited: Dec 4, 2004
  2. jcsd
  3. Dec 4, 2004 #2


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    Is it the first molecule on the zip file?
  4. Dec 4, 2004 #3


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    Yes, the compound is the first, I mean, the leftmost one. I think I will change my route to thiourea synthesis, and I think I can synthesize it via the amine+thiophosgene, and do the rest.
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