Re: ORGLIST: Chlorination of primary amino alcohols

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From: Manjunath Channapur (channapur$##$gmail.com)
Date: Thu Oct 25 2007 - 00:33:23 EDT


dear chamula
i am not that experience in halogenation or synthesis,but my opnion is
doing chlorination to alcohol getting back starting material indicates u can
avoid usual work-up if reaction proceeded (how u confirmed?) i.e do work-up
under inert atomsphere or avoid moisture.
U can just take reaction mass for further step after distilling excess
thionyl chloride and finally coevoporate this with benzene ,toluene xylene
etc to remove traces.
Good luck
Regards
Manjunath B C
Scientist-Medcinal Chemistry
Connexios Lifescience
Bangalore

On 10/24/07, J.R.Munoz <chamula$##$cybercable.net.mx> wrote:
>
> I've been working on some coupling agents in my biochemistry project and
> have a need to chlorinate phenylalaninol, I've tried thionyl chloride in
> excess molar equivalent in chloroform , there allowing for reflux of 2
> hours
> as some literature suggests....however after I tried to remove the
> chlorinated material with ethylacetate as a precipitate but then when I
> did
> a tlc I found much of the starting alcohol mark as well as a higher mark,
> presumably the halogenated material.
> Why did the material not halogenate(chlorinate) .....is there someone with
> experience with the halogenation (chlorinaion) of this particular amino
> alcohol that can assist me.....thanks in advance.
>
>
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-- 
Manjunath

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