First of all, thank you for reading my question. There is a mechanism I read where the pyrrole reacts with its C2 but I can't draw the arrows so I don't know if I am correct to think that :

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the ester: is a deactivating group because it has a Mesomeric electron-withdrawing effect (M-) so it deactivates the C4 the methoxy: is an activating group because of its electron-donating effect (M+) so it activates the C4

--> and M+>M- so it will react on C4

But the pyrrole likes to react on its C2 but it is deactivated by the ester (because in para)

Please explain me how does it work I am very lost...

  • $\begingroup$ All of your mesomeric effects may serve to slow the rate of the reaction but reaction occurs as shown. $\endgroup$
    – user55119
    Sep 21 at 22:56
  • $\begingroup$ Actually I think I understood why I was lost, because I was thinking of the reaction like it is SEar but here it's in SNar, right ? $\endgroup$
    – Mimi
    Sep 22 at 14:00
  • $\begingroup$ It sounds to me that you are memorizing too much and not going with the facts. You're given the answer. Now "push mechanistic arrows" accordingly. $\endgroup$
    – user55119
    Sep 22 at 18:38


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