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Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
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Topic: Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol) (Read 2395 times)
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smalhotr
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Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
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on:
October 09, 2015, 01:42:43 PM »
I was wondering if any one has had success in halogenating a hydroxyl group on an aromatic ring.
I am currently stuck at the step where I need to halogenate the two OH groups.
Any suggestions?
Link to Structure:https://pubchem.ncbi.nlm.nih.gov/compound/11469114#section=Top
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kriggy
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Re: Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
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Reply #1 on:
October 09, 2015, 03:45:25 PM »
Well I think this isnt going to work. You might find some metal catalyzed reaction that might work but without that, you have highly deactivated system towards aromatic nucleophilic substitution.
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smalhotr
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Re: Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
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Reply #2 on:
October 09, 2015, 05:04:00 PM »
Hmm, I see what you mean. What about halogenating the remaining unsubstituted carbons and somehow removing the OH? good ol' symmetry.
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kriggy
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Re: Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
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Reply #3 on:
October 10, 2015, 06:39:22 AM »
Good thought but Im not realy sure if there are any methods to remove thy OH group from aromatic ring
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orgopete
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Re: Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
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Reply #4 on:
October 10, 2015, 09:17:04 AM »
So, you want 2,3-dichloro-1,4-dimethylbenzene,
http://www.chemsynthesis.com/base/chemical-structure-11581.html?
You can buy it,
http://www.molbase.com/en/name-2,3-dichloro-1,4-dimethylbenzene.html
. Since it isn't novel, you could use that method to prepare your desired compound.
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smalhotr
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Re: Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)
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Reply #5 on:
October 10, 2015, 12:21:55 PM »
Thanks for all your responses.
Just in case you guys were curious, i figured out a way to halogenate the remaining unsubstituted carbons and remove the OH's using the following synthesis:
http://www.sciencedirect.com/science/article/pii/S004040200601862X
I'm going to give it a shot and see how that goes.
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Synthetic: HALOGENATING a "-OH" group on a aromatic ring. (3,6-Dimethylcatechol)