Re: ORGLIST: Chlorination of primary amino alcohols

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From: Russ Hillard (Russ.Hillard$##$symyx.com)
Date: Wed Oct 24 2007 - 17:01:03 EDT


Using DiscoveryGate to search for this chlorination retrieves reported
reaction using thionyl chloride in CHCl3 at 60 deg C for 5 hours. Check Tet
Lett (1994) 4831-4834

Russ Hillard, PhD
Sr Product Manager, DiscoveryGate
SymyxTechnologies, Inc.
2440 Camino Ramon
Suite 300
San Ramon, CA 94583

Phone: 925 543 7586
Fax: 925-543-7503
Email: Russ.Hillard$##$Symyx.com

-----Original Message-----
From: everybody-bounces$##$orglist.net [ <mailto:everybody-bounces$##$orglist.net>
mailto:everybody-bounces$##$orglist.net] On Behalf Of J.R.Munoz
Sent: Wednesday, October 24, 2007 10:04 AM
To: everybody$##$orglist.net
Subject: ORGLIST: Chlorination of primary amino alcohols

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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