ORGLIST: Bromination

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From: Jeremy M. Carr (carr030$##$bama.ua.edu)
Date: Wed Jun 06 2007 - 12:14:32 EDT


>

Try NBS in either CCl4 or cyclohexane at reflux. I tried it on a
ketone before and got quant. yield; the best part is that the
resultant succinimide isn't very soluble in either solvent. Also,
remember to recrystallize your NBS from water before the reaction (if
it's yellow, it's tainted w/ bromine and you'll risk over-
bromination.. I just learned that the hard way)

Good luck,

-J

> Hi all:
>
> I need to brominate the acetyl group of
> 4-acetyl-2,6-di-t-butylphenol
> [3,6-di-t-butyl-4-hydroxyacetophenone]. Tried bromine
> in ether with/without light or AlCl3 and also with
> CuIIBr2 in EtOAc. Only partial bromination. One
> russian patent mentions bromination at 120 oC in
> n-octane under light bulb. Any
> alternatives/suggestions?
> Thanks in advance
>
> KN Rajasekharan PhD
> Prof Chem
> Univ Kerala

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