Bromination of methoxy acetophenone?

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:- [Only registered users see links. ]

Darren Rhodes wrote:

Methylation of a phenol - in acetone + K2CO3, add dimethyl sulphate.

--
Ron Jones

Don't repeat history, see unreported near misses in chemical lab/plant
at [Only registered users see links. ]

"Darren Rhodes" <[Only registered users see links. ]> wrote in message
news:bvrbeq$gg2$[Only registered users see links. ]...

*methoxy anisoles:*
or *even methoxy acetophenones*

I
the
[Only registered users see links. ]

You may want to use NBS (N-bromosuccinimide) or dibromohidantoine
(very similar to NBS, but has 2 active bromines per molecule). Those
reagents do not produce HBr.

Now, you can brominate both the methyl ketone part or the
methoxy-phenyl ring. De-methylation should not be a problem with NBS.
What gets brominated may be controlable by the used reaction
conditions.

I cannot read SMILE notation. What isomer do you have (o, m, p-
methoxy?)
Where do you want to brominate - methylketone or the ring? If ring,
where to?





"Darren Rhodes" <[Only registered users see links. ]> wrote in message news:<bvrbeq$gg2$[Only registered users see links. ]>...

"Muhammar" <[Only registered users see links. ]> wrote in message
news:a6cffac9.0402041531.1f5e434e@posting.google.c om...

Hi Muhammar

Thanks for the reply. I've used dibromohydantoin a couple of times in the
past. I'll look into the conditions necessary to use this reagent ...

If you cut and paste the smiles string into the daylight webpage
[Only registered users see links. ] you'll see the structure of the
compound. However, I posted the structure simply to illustrate the point
rather than to give the structure of the actual compound that I am thinking
about preparing.

Darren.




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will
the
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