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imrober
A really tough bot, or a member.
Joined: 22 Jun 2006
Posts: 2
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 Posted: Thu Jun 22, 2006 11:35 pm Post subject: fluorine addition |
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Hi,
I have something I'm concerned about. I'm trying to come up with a method for fluorination of an aniline ring. I would like to fluorinate the amino so that the product is Aryl-NHCH2CF3, for example. Does any one know if trifluorobromoethane could be used to synthesize the above product? If not is there another reagent I could use?
Thanks,
IR
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logeshchem
Junior Member
Joined: 24 Aug 2006
Posts: 5
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| Posted: Thu Aug 24, 2006 5:17 am Post subject: Alkylation, and not fluorination. |
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I'm afraid you're wrong in saying "you fluorinate it to the triflouro alkyl derivative". What you do in the process you've described is you alkylate; the alkyl group has 3 flourines in it.
There maybe a competing effect, too. You have 3 Fs and a Br. Decide which one is stronger. If you turn out to have Br as the stronger of the two towards the H of NH2 of aniline, you have the alkylation done successfully. Otherwise, you will have to go for other reactants.
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logeshchem
Junior Member
Joined: 24 Aug 2006
Posts: 5
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| Posted: Thu Aug 24, 2006 6:52 am Post subject: Another method |
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[color=blue]Hi, there's another method you may use to synthesize the desired compound.
Aniline + CF3COCl ---> C6H5NHCOCF3
The amide formed can be reduced with the use of LiAlH4 to obtain the amine, or the end product C6H5NHCH2CF3.
The second step is just hydride transfer from the hydride to the N-substituted amide.
[/color]
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| For the second step, you may look at p750 of Bruice's Organic Chemistry. 3e. |
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