January 15, 2025, 07:00:28 AM
Forum Rules: Read This Before Posting


Topic: 5-fluro-2-oxindole synthesis from 2-chloro-N-(4-flurophenyl) acetamide  (Read 412 times)

0 Members and 1 Guest are viewing this topic.

Offline Rahul Bhujbal

  • Very New Member
  • *
  • Posts: 2
  • Mole Snacks: +0/-0
Please suggest any strong lewis acid (except AlCl3) or catalyst that can promote the intramolecular friedal crafts cyclization of 2-chloro-N-(4-fluorophenyl) acetamide

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 5724
  • Mole Snacks: +332/-24
Re: 5-fluro-2-oxindole synthesis from 2-chloro-N-(4-flurophenyl) acetamide
« Reply #1 on: January 02, 2025, 08:32:20 PM »
What are your thoughts?

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 2315
  • Mole Snacks: +156/-10
Re: 5-fluro-2-oxindole synthesis from 2-chloro-N-(4-flurophenyl) acetamide
« Reply #2 on: January 05, 2025, 12:04:23 AM »
Any Lewis acid will bind to the amide oxygen/nitrogen and inactivate the aromatic nucleus, I don't see how this could work. Do you have any alternative scheme?

Offline Rahul Bhujbal

  • Very New Member
  • *
  • Posts: 2
  • Mole Snacks: +0/-0
Re: 5-fluro-2-oxindole synthesis from 2-chloro-N-(4-flurophenyl) acetamide
« Reply #3 on: January 05, 2025, 02:03:40 AM »
Any Lewis acid will bind to the amide oxygen/nitrogen and inactivate the aromatic nucleus, I don't see how this could work. Do you have any alternative scheme?
No there is no alternative this is the reported scheme, in which AlCl3 is used as lewis acid which takes out the chlorine and results in the formation of carbocation which then binds with the aromatic ring carbon and forms the oxindole ring

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 2315
  • Mole Snacks: +156/-10
Re: 5-fluro-2-oxindole synthesis from 2-chloro-N-(4-flurophenyl) acetamide
« Reply #4 on: January 06, 2025, 11:33:34 PM »
Ok, why don't you like AlCl3? It's cheap?

Sponsored Links