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Natural Science Forum / Chemistry / Organic Synthesis / February 2004



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Bromination of Acetophenone anisoles ...

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Darren Rhodes - 06 Feb 2004 21:53 GMT
Hello all

Anyone got any good references for the bromination of methoxy anisoles: I
want to brominate the acetophenone but I suspect the usual conditions will
remove the methyl group.  I found a reference to the reaction below but the
yield was below 50 % T and it had column chromatography as a work up.

Reaction in smiles:- COC1=CC=CC=C1C(C)=O plus bromine giving
COC1=CC=CC=C1C(CBr)=O

Any leads appreciated and I'm open to a discussion as to methylating the
phenol post bromination.

Thanks ... Darren.

ps for those unfamilliar with smiles:- http://www.daylight.com/daycgi/depict

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Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

Ian Gilmore - 20 Feb 2004 21:28 GMT
> Hello all

> Anyone got any good references for the bromination of methoxy anisoles: I
> want to brominate the acetophenone but I suspect the usual conditions will
> remove the methyl group.  I found a reference to the reaction below but the
> yield was below 50 % T and it had column chromatography as a work up.

> Reaction in smiles:- COC1=CC=CC=C1C(C)=O plus bromine giving
> COC1=CC=CC=C1C(CBr)=O

> Any leads appreciated and I'm open to a discussion as to methylating the
> phenol post bromination.
>
> Thanks ... Darren.
>
> ps for those unfamilliar with smiles:- http://www.daylight.com/daycgi/depict

If I was going to brominate an acetophenone I'd use copper bromide. I
haven't got the actual reference but looking at Larock it may be JOC
27 4397 (1962).
Uncle Al gave the recipe a while back.
Bromoacetophenones can be very lachrymatory!
Ian
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Paul J. Franklin(moderator - sci.chem.organic.synthesis)
http://organicworldwide.net/sci.chem.organic.synthesis
Georgia State University <chepjf@panther.gsu.edu>
Atlanta, GA

 
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