> The paper seems to suggest that the PdCl2 is regenerated.
In theory it should be. But looking at their yields and the amounts of CuCl2 employed makes me believe not much catalyst regeneration is taking place. This procedure definitely needs some additional work.
> 1. Brominate the 5 position
> 2. Convert to 3-meo-4,5-hydroxy phenylacetone with Cu or CuBr
> 3. Methylate with DMS or MeI to 3,4,5-trimethoxy phenylacetone
> [cf. mescaline from vanillin @ Rhodium's]
Let me suggest the following procedure:
1. Perform this reaction in an alcoholic solvent (MeOH, EtOH, or ethandiol)
2. Isolate the ketal, since it is more stable in the following reactions
3. Convert to the diphenol, or better yet syringylketone
4. alkylate the 4 position (lots of interesting possibilities)
Maybe stuff like 3-MeO-4-allylamphetamine or 3-MeO-4-EtO-amphetamine will be a worthwhile target for some, so let's not forget about these potentially interesting compounds.
I'm not fat just horizontally disproportionate.