ORGLIST:Benzylic Halogenation

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From: Devin Pantess (pantess$##$bellsouth.net)
Date: Wed Jun 02 2004 - 20:53:05 EDT


Hello All,

I need to make an a-chloro (or bromo, chloro preferred) derivative of o-toluyl
chloride, a-chloromethyl toluyl chloride. My question is this: Is there an
easier way than using Cl2 to make this compound? I have found using
Phthalide and SOCl2, along with some type of catalyst. The problem is that
the prep comes from a patent source, and the language is very vague. Would
NCS work here on the already active benzylic position of o-toluyl chloride,
or will I just have to bubble Cl2 gas (nasty) through the soln for 24 hours
(even worse!) Please help!

Thanks in advance.

Devin

PS The bromo derivative would probably be too reactive for what I am going to
use thi sproduct for, lets just say the following reaction would be more or
less instantaneous, but not what I want. Br2 and a tungsten lamp for 2 hrs
will get me the bromo derivative.
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