Question

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.

Answer 1

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)