Bromovanillin

[LiquidGaia]

SWIM was thinking of making bromovanillin using oxone and NaBr.  Under one of chromic's threads oxone is used to make Br2. SWIM's wondering if this could be done in one pot.

ie.

vanillin and oxone, and NaBr are placed in a Methanol solution.  Would SWIM be able to get bromovanillin?

also what would the bp of bromovanillin, hydroxyvanillin and 3,4,5-tmba be?
(SWIM's planning on distillation after each rxn step.)

thx.

[Rhodium]

5-Bromovanillin, mp 164°C (No bp listed in beilstein)

5-Hydroxyvanillin, mp 132°C (No bp listed in beilstein)

3,4,5-Trimethoxybenzaldehyde, mp 77°C

3,4,5-Trimethoxybenzaldehyde, bp 163-165°C/10mmHg, 158-161°C/7-8mmHg, 148-151°C/5mmHg, 136-138°C/4mmHg, 130°C/0.5mmHg

[LiquidGaia]

how would one go about seperating the bromovanillin from the rest of products that will form from the reaction?

[Rhodium]

Have you even read this:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/mmda.mescaline.html

[LiquidGaia]

yeah I have, although I'm not sure if I want to work with Br2 in gas form.

I was planning on making the gas via NaBr H2SO4 then H2O2 if I could do it in solution and without the need for GAA (expensive) I'd prefer that route.

[Rhodium]

Br₂ is not a gas, and what I was referring to was that the document contains explicit directions for purification if all the intermediates. You will also find a whole bunch of posts on this issue using the search engine.

[LiquidGaia]

wow, I truely need to do a lot more studying before I attemp the synth, everything is theory right now (I'm not a chemist, currently a student).  but thanks, I'll look into the purification, I actually have it saved.

Thank for the help Rhodium.

[Aurelius]

Hey LiquidGaia, if you have specific questions to ask, you can feel free to ask aurelius in a pm.