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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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Assignment Expert
15.11.12, 14:17

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<p class="MsoNormal"><span style="font-size:11.5pt;font-family:"Arial","sans-serif";
mso-fareast-font-family:"Times New Roman"">The most important condensed ring
system related to these heterocycles is indole. Some electrophilic substitution
reactions of indole are shown in the following diagram. Whether the indole
nitrogen is substituted or not, the favored site of attack is C-3 of the
heterocyclic ring. Bonding of the electrophile at that position permits
stabilization of the onium-intermediate by the nitrogen without disruption of
the benzene aromaticity.&

You must& combine the indole, carbonyl chloride (RCOCl), and Aluminum
Chloride (AlCl3) or dialkylaluminum cloride(Lewis acids) as a catalyst under
anhydrous conditions. (t=0 degree C).</span><span style="mso-fareast-font-family:
"Times New Roman""></span></p>

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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?

Assignment Expert
12.11.12, 18:12

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the DMSO has a high boiling point, you can drive away it from the solution on a
rotary evaporator, where yuo can pump vacuum and control temperature of water
bath. Decreasing pressure halves the boiling point of about 15 degrees Celsius</span></p>

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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?

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