3,4-MD-phenyl-2-nitropropene is then reduced to MDA
Title: That reaction qould be very low yielding, if ...
Post by: Rhodium on October 29, 2002, 01:57:00 PM
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.
Title: Sorry Rhodium i dont quite follow.
Post by: WHITE_DEVIL on October 29, 2002, 02:31:00 PM
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?
Title: The Azide Route
Post by: Rhodium on October 29, 2002, 05:26:00 PM
Title: bad leaving group
Post by: pHarmacist on November 01, 2002, 07:42:00 AM
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.
Title: Generally halo atom on safrol is a bad bad ...
Post by: Rhodium on November 01, 2002, 09:42:00 AM
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.