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Author: Subject: obtaining a substituted benzylchloride
Cloner
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[*] posted on 10-4-2006 at 04:44
obtaining a substituted benzylchloride


I need to get a molecule which is basically a benzylchloride, only with R instead of H next to the chloride atom. Anyone have an idea how? Would grignard of bromobenzene and some aldehyde do the trick? I want the chlorine on a secondary carbon, not a tertiary...
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flyingbanana
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[*] posted on 10-4-2006 at 13:27


not exactly sure if this is what you want
but for a simple R you could do friedel crafts acylation of benzene, reduce carbonyl to alcohol and do chloride substitution there
for a more complex R, grignard with Br-R on benzaldehyde, then do chloride substitution on the resulting alcohol
SOCl2 would probably be good for the substitution
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jack-sparrow
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[*] posted on 13-4-2006 at 04:57


Cloner : You are right. Let's say you want to make 1-phenyl-1-chloropropane. You do the grignard of Bromobenzene and react with propionaldehyde. The resulting secondary alcool is treated with HCl to yield the corresponding chloride.



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