Answer to Question #18155 in Organic Chemistry for Sean

Question #18155

I have a carboxy chloride (RCOCl), and I want to attach the carbonyl group to the 3-position of indole. The N at the 1-position already has a side chain attached. How do I attach the carbonyl to the 3-position carbon? Do I have to use a Grignard reagent, such as CH3MgBr? From what I understand, the 3-carbon is highly susceptible to electrophilic substitution. Please let me know the reagents, supplies, and steps necessary.

Expert's answer

This might be more simpler with a Friedel-Crafts acylation. Since the 3-carbon position on indole is the most highly reactive, binding to that site shouldn't be a problem. But I think I need to combine my indole, carbonyl chloride (RCOCl), and Aluminum Chloride (AlCl₃) or dialkylaluminum cloride (Lewis acids) as a catalyst under anhydrous conditions. (t=0)

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Sean

12.11.12, 20:29

Finally, I need to purify the final product, which involves removal of AlCl3 from the solution. How is this achieved? Is there a method to first remove the AlCl3 before evaporation into dry powder?

Sean

08.11.12, 19:35

Under anhydrous conditions, what would be the proper solvent? Either DMSO or diethyl ether? I think DMSO would be safer to use, but evaporation/purification of the final product may be a challenge, since DMSO has a high boiling point (170C). How do you evaporate DMSO?

Answer to Question #18155 in Organic Chemistry for Sean

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