Rebeka Posted April 23, 2019 Share Posted April 23, 2019 Hello everyone! I was wondering if anyone could help me with a functional group formation and curly arrow mechanism. On the drug Ibrutinib there is what I think is a diphenyl ether. I know that the Williamson Synthesis can be used to form ether but I do not understand how to form a diphenyl ether at all. I tried looking up the Ullmann synthesis but I am not sure if that would be the correct way to form a diphenyl ether. Could anyone please show me how/ what reaction would occur that would form a diphenyl ether on Ibrutinib? Any help or suggestions would be very much appreciated. Thank you! http://www.chemspider.com/Chemical-Structure.26637187.html I have attached an image of Ibrutinib in the URL above Link to comment Share on other sites More sharing options...
BabcockHall Posted April 24, 2019 Share Posted April 24, 2019 My understanding of the Ullmann reaction is limited, but it appears to be a way to make biaryl compounds. Relative to what you want, the product is missing the oxygen. Can you explain why you think that the Williamson synthesis might not work in this instance? Link to comment Share on other sites More sharing options...
Rebeka Posted April 24, 2019 Author Share Posted April 24, 2019 I have been told the Williamson synthesis would not work to form the ether I need because diphenyl ether is an aryl halogen. Beyond that my understanding of why it will not work its very limited. I know you can form an ether from a benzene ring, but I do not understand how to form an ether with two phenyl/aryl groups as the R groups. Does anyone know the reaction mechanism that I would use to form the ether on Ibrutinib? https://www.youtube.com/watch?v=CnZQiHgnuok I tried using this as a template for the reaction, but I'm honestly not sure if I'm on the right path here Link to comment Share on other sites More sharing options...
hypervalent_iodine Posted April 25, 2019 Share Posted April 25, 2019 Are you actually trying to make this? Link to comment Share on other sites More sharing options...
Rebeka Posted April 25, 2019 Author Share Posted April 25, 2019 No, it is just for a project to show a possible reaction mechanism to form it. Link to comment Share on other sites More sharing options...
hypervalent_iodine Posted April 25, 2019 Share Posted April 25, 2019 There are a few ways. Ullman, as you suggested, Buchwald Hartwig coupling, or Chan Lam. Organic portal has an overview of these, plus literature examples. https://www.organic-chemistry.org/synthesis/C1O/biarylethers.shtm Link to comment Share on other sites More sharing options...
BabcockHall Posted April 25, 2019 Share Posted April 25, 2019 @OP, The Williamson ether synthesis is usually given as an example of SN2 chemistry in introductory organic chemistry. Aryl bromides or aryl iodides are unreactive in SN2 reactions. Why do you suppose that is the case? Link to comment Share on other sites More sharing options...
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