Benzyl bromide references needed...
I'm looking for any references to the photocatalytic bromination of toluene.
I imagine its very similar to that of benzyl chloride, but I'd like to know if there is some more specific information out there on the mechanics of
the reaction.
Edited to add:
There is a reference to the production of benzyl bromide in "The War Gases" in the board library. 50 grams of toluene in a dry flask, slowly drip in
75 grams of bromine out in the sun, and your done.
Sounds just too convenient. I suppose it would be OK for a war gas, however I'd like to see if it can be turned into benzaldehyde by refluxing with
sodium nitrate. An extra bromine on the methyl group would not be good for the reaction, nor would any nuclear substitued by-products.
Curiously enough, there are some scant references to the fact that bromine will not attach directly to the ring unlike chlorine and is 100% selective
to the alpha position. I haven't seen this in a direct bromination references, but some references to this were made in reactions calling for
N-bromosuccinimide.
If both create free radicals, then it shouldn't matter one way or the other, its just that the N-bromosuccinimide is a convenient source of bromine.
[Edited on 3-7-2006 by evil_lurker]
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