Formula409
Hazard to Others
Posts: 129
Registered: 13-12-2008
Member Is Offline
Mood: No Mood
|
|
3-methoxy-4-bromobenzaldehyde
Trying to find or come up with some sort of preparation of this compound. I've found references for several of the steps I have proposed, but some
references don't deal with the specific compounds.
Here is the proposed route from toluene:
The only step I am unsure of as of now is that nitration and where the group would go. Unsubstituted benzaldehyde gets substituted primarily in the
meta position, however I am unaware as to what effect the bromine atom has. I've thought about whether it is possible to nitrate m-hydroxybenzaldehyde
at the para position, reduce to an amine and then swap the amine for a bromine atom by this procedure: http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1...
however I am once again unsure as to where the ring would be substituted, presumably not in the para position, but the other meta position.
Can you guys suggest any improvements/potential problems with the routes that I have selected? I have no access to literature searches so obviously my
only information sources are patents and the extensive Rhodium archive. I'm trying to do this with (relatively) available materials.
If anyone has more specific references, then I am more than happy to hear, well read them!
Refs:
[1] http://www.sciencemadness.org/talk/viewthread.php?tid=6882
[2] http://www.sciencemadness.org/talk/files.php?pid=86142&a...
[3] http://www.orgsyn.org/orgsyn/prep.asp?prep=CV2P0089
[4] http://www.erowid.org/archive/rhodium/chemistry/aromatic.bro...
[5] http://www.sciencemadness.org/talk/viewthread.php?tid=11720#...
[6] http://www.erowid.org/archive/rhodium/pdf/phenol.nitration.p...
[7]Vogel’s
[8] http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2...
I can post more detailed procedures, however why regurgitate already published procedures?
Formula409.
[Edited on 5-9-2009 by Formula409]
|
|
|
Formula409
Hazard to Others
Posts: 129
Registered: 13-12-2008
Member Is Offline
Mood: No Mood
|
|
Edit: Can this please be moved to the "organic chemistry" forum? I was going to post it here before I did some peeking around!
Formula409.
|
|
|
Klute
International Hazard
Posts: 1378
Registered: 18-10-2006
Location: France
Member Is Offline
Mood: No Mood
|
|
None of your brominating refs are revelant: no where is benzaldehyde brominated. It will not brominate at the para position.
Bromination of 3-methoxybenzaldehyde should give your seeked product. This aldehyde can be prepared by methoxylation of m-bromobenzaldehyde, the
product obtained by carefull bromination of benzaldehyde.
A lengthy way from vanillin would be the following: turn the phenol into an amine (http://www.freepatentsonline.com/5214210.html), hydrolyze the formed aldimine, diazotize and react with CuBr. Should work, might need to check the
amination procedure as the conditions might be a bit harsh for the aldehyde.
Otherwise formylation of 2-bromoanisole will give a mixture of isomers, your product being the minor one I suppose.
[Edited on 5-9-2009 by Klute]
\"You can battle with a demon, you can embrace a demon; what the hell can you do with a fucking spiritual computer?\"
-Alice Parr
|
|
|
Formula409
Hazard to Others
Posts: 129
Registered: 13-12-2008
Member Is Offline
Mood: No Mood
|
|
| Quote: | None of your brominating refs are revelant: no where is benzaldehyde brominated. It will not brominate at the para position.
|
My mistake, however brominating toluene and then oxidising should be find should it not?
| Quote: |
Bromination of 3-methoxybenzaldehyde should give your seeked product. This aldehyde can be prepared by methoxylation of m-bromobenzaldehyde, the
product obtained by carefull bromination of benzaldehyde.
|
According to the attached paper, iodination of 3-methoxybenzaldehyde yields 3-methoxy-6-iodobenzaldehyde. Nichols says that bromination of
m-hydroxybenzaldehyde gives 2-bromo-5-hydroxybenzaldehyde [9].
| Quote: |
A lengthy way from vanillin would be the following: turn the phenol into an amine (http://www.freepatentsonline.com/5214210.html), hydrolyze the formed aldimine, diazotize and react with CuBr. Should work, might need to check the
amination procedure as the conditions might be a bit harsh for the aldehyde.
|
Vapour-phase sounds a bit out of the question though.
[9]http://www.erowid.org/archive/rhodium/chemistry/bromomethoxyamph.nichols.html
I'll update the original post in order to correct my mistake. Thanks for pointing that out!
Formula409.
[Edited on 5-9-2009 by Formula409]
Attachment: iodinations.pdf (74kB)
This file has been downloaded 688 times
|
|
|
Polverone
Now celebrating 21 years of madness
|
Threads Merged
7-9-2009 at 19:49 |
![[*]](images/xpblue/default_icon.gif){kind=icon}
