10-29-02 12:18
No 374180
This sounds so simple that im sure it cant work but here goes:
bromosafrole + NaNO2 => 3,4-MD-phenyl-2-nitropropene + NaBr
3,4-MD-phenyl-2-nitropropene is then reduced to MDA
(Chief Bee)
10-29-02 13:57
No 374242
That reaction qould be very low yielding, if nitrite at all would react with a secondary halide - and if it would, mostly the nitrite ester would be formed. Swap bromosafrole with azide instead, with that almost quantitative yields are possible.
(Newbee)
10-29-02 14:31
No 374256
Sorry Rhodium i dont quite follow. Do you mean react sodium azide with bromosafrole. or fuck bromosafrole right off and actually start with 3,4-MD-phenyl-2-azidopropene. how would you go about doing this?
(Chief Bee)
10-29-02 17:26
No 374311
I meant:
Safrole -> Bromosafrole -> Azidosafrole -> MDA
../rhodium /mda.azi
Also UTFSE for azide and bromosafrole.
(Hive Bee)
11-01-02 07:42
No 375384
Generally halo atom on safrol is a bad bad leaving group, however, wouldn't it be more conveniant to simply "oxymercurate" safrol to corresponding sec. alcohol, followed by mesylation, that would convert OH (bad leaving group) to one of best leaving groups, this can then be attacked by a nucleophile such as methylamine in sn2 fashion... the only problem is if not 2 different mechanisms (sn2/E2) will take place one (sn2) leading to MDMA and (E2) leading to isosafrol + H2O :), this of corse can be controlled (kinetic/thermal) controll.... i dunno, just a thought..
Never underestimate the power of retrosynthesis.
(Chief Bee)
11-01-02 09:42
No 375410
Generally halo atom on safrol is a bad bad leaving group
Why? With a PTC you can get close to quantitative yields in the SN2 rxn between azide and bromosafrole.
wouldn't it be more conveniant to simply "oxymercurate" safrol to corresponding sec. alcohol
It works, but I would hardly call that route more convenient in any way, also you need a stoichiometric amount of mercury salt when oxymercurating safrole, which is almost twice the weight of Hg salt to safrole.