I've been looking at an alternate route to synthezing phenethylamines, not the classic aldahyde-->nitroethene-->amine route.
Assuming one were to start with 1,4-dimethoxybenzene here are two of the routes.
I.
A. 1,4-dimethoxybenzene is brominated via NBS to give a 1-bromo-2,5-dimethoxy benzene.
B. An allybenzene grignard reagent is added to the 1-bromo,2-5-dimethoxybenzene to give a 2,5-dimethoxyallybenzene compound.
from:(
https://www.thevespiary.org/rhodium/Rhodium/chemistry/safrole.html
)
C. the 2,5-dimethoxyallybenzene is then oxidized using KMnO4/ Ozone/ H2O2 to give the corresponding phenylacetylaldahyde.
D. the aldahyde is reacted with hydroxylamine, to give the oxime and the oxime reduced to the amine.
from: (
https://www.thevespiary.org/rhodium/Rhodium/chemistry/allylbenzene2phenylacetaldehyde.html
)
the other idea was to use a Friedel-Craft type rxn to get the allybezene formed by using allyl bromide and AlBr3.
The only concern I have is the allyl bromide reacting with its self? (will this occur?).
Any criticism would be appreciated.
Thanks.