synthesis of 5-bromovanillin

This is very easy and nice synthesis of 5-bromovanillin an important precursor for syringaldehyde.

The vanillin smells really nice but the bromo derivate has almost no smell at all, which is quite interesting, cause in my experience bromo derivates usually have quite strong smell

Category:

Science & Technology

Tags:

• 5-bromovanillin
• vanillin
• synthesis
• syringaldehyde
• organic
• chemistry
• chemx01
• bromine
• methanol

[jthouse51]

making mescaline?

[chemx01]

@jthouse51 Absolutely not, I hate drugs and they make bad name of every home chemist anywhere. I just want to try some synthesis with vaniline which I got for free, and yes I made 3,4,5-trimethoxybenzaldehyde, but only because I wanted to practise anhydrous work and I really enjoy working with vaniline, such a beautifull smell :-).

And before anyone asks no, I'm not going to post the 3,4,5-trimethoxybenzaldehyde synthesis because I haven't analyzed the product yet.

[TC8361]

@TC8361 MeI posted and I'm curious if this what you used. I can't imagine your yields would have been too good, but I may be wrong and would certainly like to hear the details.

Keep up the good work!

Tony.

[TC8361]

Do you recrystallize your final product? I've only done this in GAA, 15.6g batches of vanillin consistently yield 22g bromovanillin, but there is always 2-4g unreacted vanillin in the final product, really throws off the M.P., but easily removed by a re-x from denatured ethanol, final M.P. is 160-163. I'm curious if there is as much unreacted vanillin if done in MeOH.

You say you went to 3,4,5-TMB? Did you manage to methylate your methoxy/hydroxy product with MeI? I see you have a prep of...

[LeinAlex]

So is it true 5-bromovaniline? Is it not colorless product? Seems like bromine is in ready substance.

[DoktorKlawonn]

Purity? Melting point?

[aaronjhard]

Nice synthesis dude, !!!!

[pyrochemik]

velmi pekne a ake ma bromvanilin pouzitie?