Can 4,5-Dibromoisatin Be Synthesized?

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In summary, the conversation discusses the synthesis of a chemical compound and considers using 1,2-dibromobenzene as a starting material. The potential steps include nitration, reduction, tosylation, Friedel-Crafts alkylation, and deprotection to form the desired amine compound. The possibility of using other dibromo isomers and alternative synthesis routes are also mentioned.
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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.

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 http://themerckindex.cambridgesoft.com/TheMerckIndex/NameReactions/onr354.htm 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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  • #2
Is it the first molecule on the zip file?
 
  • #3
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.
 

1. What is the purpose of synthesizing 4,5-Dibromoisatin?

The purpose of synthesizing 4,5-Dibromoisatin is to obtain a compound that has potential biological and medicinal properties, such as anticancer and anti-inflammatory effects.

2. What is the chemical structure of 4,5-Dibromoisatin?

The chemical structure of 4,5-Dibromoisatin is C8H4Br2N2O2. It consists of two bromine atoms attached to the benzene ring and a carbonyl group attached to a nitrogen atom.

3. What are the key steps involved in the synthesis of 4,5-Dibromoisatin?

The key steps involved in the synthesis of 4,5-Dibromoisatin are the bromination of isatin, followed by the condensation of the resulting 5-bromoisatin with 4-bromobenzaldehyde, and finally, the oxidation of the intermediate to yield 4,5-Dibromoisatin.

4. What are the common methods used for the synthesis of 4,5-Dibromoisatin?

The common methods used for the synthesis of 4,5-Dibromoisatin include the Sandmeyer reaction, the Vilsmeier-Haack reaction, and the Bucherer-Bergs reaction. These methods involve the use of different reagents and conditions to obtain the desired product.

5. What are the potential applications of 4,5-Dibromoisatin?

Some potential applications of 4,5-Dibromoisatin include its use as an intermediate in the synthesis of various organic compounds, as well as its potential use in the development of new drugs for the treatment of diseases such as cancer and inflammation.

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