Can 4,5-Dibromoisatin Be Synthesized?

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SUMMARY

The synthesis of 4,5-Dibromoisatin can be achieved through a retrosynthetic analysis involving 1,2-dibromobenzene, which can be nitrated to form a nitro derivative. This compound is then reduced to an amine, tosylated, and reacted with 1-chloroethylene glycol via Friedel-Crafts alkylation. The tosyl group can be deprotected, or alternatively, the compound can be oxidized with acidic permanganate to yield a ketoacid before deprotection. The discussion also explores alternative synthesis routes, including thiourea synthesis and comparisons with established methods like Sandmeyer's reaction.

PREREQUISITES
  • Understanding of Friedel-Crafts alkylation
  • Knowledge of tosylation and deprotection techniques
  • Familiarity with nitration and reduction reactions
  • Experience with oxidation reactions using acidic permanganate
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  • Research Friedel-Crafts alkylation mechanisms and conditions
  • Study tosylation and its applications in organic synthesis
  • Learn about the use of acidic permanganate for oxidation reactions
  • Investigate thiourea synthesis methods and their advantages
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Chemists, organic synthesis researchers, and students interested in advanced organic synthesis techniques and methodologies for synthesizing complex compounds like 4,5-Dibromoisatin.

chem_tr
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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.<br /> <br /> 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.<br /> <br /> Thank you for your interest.<br /> <br /> P.S. I have seen that there are better ways like <a href="http://themerckindex.cambridgesoft.com/TheMerckIndex/NameReactions/onr354.htm" target="_blank" class="link link--external" rel="nofollow ugc noopener">http://themerckindex.cambridgesoft.com/TheMerckIndex/NameReactions/onr354.htm</a> 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.[/tex]
 

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Is it the first molecule on the zip file?
 
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.