- fluorine addition

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imrober

June 22nd, 2006 18:35

fluorine addition

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

logeshchem

August 24th, 2006 00:17

Alkylation, and not fluorination.

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.

logeshchem

August 24th, 2006 01:52

Another method

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.

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