Dismiss Notice
Join Physics Forums Today!
The friendliest, high quality science and math community on the planet! Everyone who loves science is here!

4,5-Dibromoisatin synthesis

  1. Dec 4, 2004 #1


    User Avatar
    Science Advisor
    Gold Member

    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.

    Attached Files:

    Last edited by a moderator: Apr 21, 2017
  2. jcsd
  3. Dec 4, 2004 #2


    User Avatar
    Science Advisor
    Homework Helper

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


    User Avatar
    Science Advisor
    Gold Member

    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.
Know someone interested in this topic? Share this thread via Reddit, Google+, Twitter, or Facebook

Similar Discussions: 4,5-Dibromoisatin synthesis
  1. COOH synthesis (Replies: 7)

  2. Tough Synthesis (Replies: 11)

  3. Benzene synthesis (Replies: 4)