chloechem
Harmless
Posts: 1
Registered: 22-5-2017
Member Is Offline
Mood: No Mood
|
|
Hunsdiecker reaction prevent bromination + bromine to methyl?
Hi, I'm using the Hunsdiecker reaction to convert [2-(Aminomethyl)phenyl]acetic acid (red) to 1-[2-(Bromomethyl)phenyl]methanamine (green). How do I
stop, or at least reduce the formation of 1-[4,6-Dibromo-2-(bromomethyl)phenyl]methanamine (blue) (or more than one bromine), and then convert the
bromine to a methyl group (1-(2-Ethylphenyl)methanamine (black)). Thank you.
[Edited on 23-5-2017 by chloechem]
[Edited on 23-5-2017 by chloechem]
|
|
|
clearly_not_atara
International Hazard
Posts: 2692
Registered: 3-11-2013
Member Is Offline
Mood: Big
|
|
This is not a wise choice of intermediate. The product will likely convert to 2H-indoline, and the formation of this side-product cannot be prevented
under the conditions of the Hunsdiecker reaction.
However, under normal Hunsdiecker conditions, ring-bromination will not be significant, and can be ignored.
But instead consider e.g. reducing the acid to an alcohol with LiAlH4
|
|
|
CuReUS
National Hazard
Posts: 928
Registered: 9-9-2014
Member Is Offline
Mood: No Mood
|
|
Why don't you directly reduce the COOH to CH3 ? http://www.sciencemadness.org/talk/viewthread.php?tid=73024#...
|
|
|
Nicodem
|
Thread Moved
23-5-2017 at 08:39 |
![[*]](images/xpblue/default_icon.gif){kind=icon}
