Would the brominating of 2,4-dimethoxyphenylethylamine freebase using 1-1,2 molar equivalent NBS as described in post Post 71830 (missing)
(Rhodium: "2C-B and 2C-C with N-halosuccinimide", Methods Discourse) work as it is?.
The post Post 506068 (https://www.thevespiary.org/talk/index.php?topic=10548.msg50606800#msg50606800)
(moo: "NBS works because it liberates Br2 when ...", Newbee Forum) describing the bromination mechanism of NBS stating that "NBS works because it liberates Br2 when reacting with HBr, which itself is usually liberated when a substrate is brominated by Br2, thus keeping the concentration of free elemental bromine low in the reaction mixture."
If this would bee true isnt it possible that the H-Br reacts with the freebase amine which would probably lower the yields when using only a 1-1,2 molar NBS equivalent?
Or does the bromination with NBS proceed as described in post Post 478637 (https://www.thevespiary.org/talk/index.php?topic=7291.msg47863700#msg47863700)
(Nicodem: "NBS generates bromine radicals that will ...", Chemistry Discourse) stating "NBS generates bromine radicals that will potentialy substitute any easily abstractable hydrogen."
Which if correct and using CH3CN as solvent should only brominate the aromatic ring.
N-Bromosuccinimide in Acetonitrile: A Mild and Regiospecific Nuclear Brominating Reagent for Methoxybenzenes and Naphthalenes
M. Carmen Carreiio,* Jose L. Garcia Ruano,* Gemama Sanz, Miguel A. Toledo, and Antonio Urbano
Departamento de Quimica Orgcinica G I ) , Universidad Autonoma de Madrid, Cantoblanco, 28049 Madrid, Spain
J. Org. Chem. 1995,60, 5328-5331
In this paper, we describe the high regioselectivity achieved in the ring bromination of several methoxy derivatives of benzene and naphthalene with NBS in CCl4 and the substantial increase in reactivity observed using acetonitrile as solvent. We also report on the exclusive aromatic ring bromination of several methyl anisoles with NBS in CH3CN, which strongly contrasts with the predominant benzylic brominationg observed for the same substrates in CCl4.
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)
Are you sure?
There must have been mixed up a couple of 5's somewhere. ;)
btw, what are you going to do with this compound? as I can see it can't yield anythig active w/o bost from MAOI.
Do you think that you can try this Post 518568 (https://www.thevespiary.org/talk/index.php?topic=7492.msg51856800#msg51856800)
(Kinetic: "Iodination of arenes with KI and H2O2", Chemistry Discourse) on the 2,4-dimethoxyphenylethylamine and report back?