Making Bromovanillin: A Precursor To Substituted Benzaldehydes

In todays video I will show you how to make bromovanillin which is a precursor to other substituted benzaldehydes. You could for example make hydroxyvanillin from it. Bromovanillin is made by dissolving vanillin in methanol and brominating it by slowly adding toxic bromine. These react and you get bromovanillin. Crash it out with water, filter, wash and you are finished.
Do NOT try this at home. The video is for educational and entertainment purposes only.
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[@THYZOID]

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[@everythingexplained3226]

why wouldn't we want 5 hydroxy vanilin, if we clicked on bromovanilin?

[@PoorMansChemist]

Make syringaldehyde. Pretty please. 😁

[@g-radical349]

whats that used for? I remember coming across it a while back while looking into iron gall ink and a few other staining compounds, but I only remember it cos the name stood out to me

[@adambruh4339]

@@g-radical349 mescaline aka 3,4,5-trimethoxyphenethylamine

[@adambruh4339]

Holy shit PoorMansChemist you’re a legend❤️

[@PoorMansChemist]

@@adambruh4339 I do my best. 😁

[@maxjoechl5663]

@@g-radical349Syringaldehyde is usually methylated to form 3,4,5-Trimethoxybenzaldehyde, from which you can make the antiparasitic trimethoprim (made infamous by 'pharma bro' Martin Shkreli).
Or… you can do a Henry reaction, reduce the resulting nitrostyrene to the amine, and form it into 75 pellets to eat with your buddy (I think his name was 'Dr Kermit') during a road trip to Las Vegas. This is also a good way to make use of any leftover ether ;)

[@SchwardsChannel]

WE GETTING DEA ATTENTION WITH THIS ONE 🗣️🗣️🗣️🗣️🗣️💯💯💯💯💯🔥🔥🔥🔥🔥

[@legenarymaster3696]

That intro was cold

[@lemmerelassal2795]

Are you going to continue this? I think sodium metal, methanol, bromovanillin together should give an interesting product.

[@THYZOID]

already did continue

[@myristicinman4566]

Marvelous stuff! Now let's demethylate the rest w/ pyridine and then add a little diiodomethane into the mix 😬😬😉

[@Quinazolineking]

Very cool

[@stilicho539]

Lol are you secretly making mescalin on a large scale?

[@TheHeavyassaulter]

Route of synthesis?

[@stilicho539]

@@TheHeavyassaulter He said he was going to make syringaldehyde from it, so after that simply: methylation, conversion to of the aldehyde to cyanide + alcohol and then reduction

[@THYZOID]

i did not say that i planned to make syringaldehyde from it. hydroxyvanillin

[@stilicho539]

​​@@THYZOIDOh I must've misremembered then. Then you could even be making 3-methoxy-4,5-methylenedioxybenzaldehyde with it lol. Anyway really great videos, keep it up! It must be hard doing organic chem without accidentally making drug precursors lol.

[@zevkurtzman8108]

​@stilicho539 that's a pretty needlessly toxic way to make phenethylamines from benzaldehydes

[@dxxrky]

Jesse, it's time to make Bromovanillin

[@chemistryofquestionablequa6252]

Great video! What did you think of the piperidone synthesis?

[@rdallas81]

Oooooh! 🎉

[@miniprime1]

Could you make a video about preparation of phthalic acid and phthalic anhydride via oxidation of naphthalene?

[@chikianglim3632]

Yes pls

[@potumnn]

FBI enters the chat

[@chemistryofquestionablequa6252]

DEA

[@zekiz774]

​@@chemistryofquestionablequa6252well he's in Germany so both won't come for him

[@crabcrab2024]

Your stupid DEA has neither authority, nor power in Europe, Gott sei Dank!

[@EddieTheH]

Wouldn't worry about it, they have no jurisdiction in Europe.

[@Raffael-Tausend]

@@chemistryofquestionablequa6252 Deutsche Erdöl Ag?
Deutsche EnsembleAkademie?

[@chemicode]

I want 1 or 2 of the mercury tilt switchs you have for an experiment if that's fine also I subscribed

[@THYZOID]

I do not sell anything. Sorry mate.

[@chemicode]

That's fine you're channel's great keep it up

[@THYZOID]

@@chemicode Thanks mate!

[@Quinazolineking]

💯

[@Exotic_Chem_Lab]

Cool

[@fano72]

Nice how the bromine is simply eaten by the vanilline. Now you have a decent amount of the end porduct. Can you substitute the bromine by an ethyl group?

[@THYZOID]

you can but it is much easier to replace with an ethoxy group. if you want an ethyl group there you must first protect a bunch of other groups

[@fano72]

@@THYZOID that's what I meant

[@ashe1.070]

Syringaldehyde or an analog thereof eventually? Does the 5-bromovanillin still smell like vanillin?

[@PoorMansChemist]

It still smelled vanilla-ish when I made it.

[@ashe1.070]

@@PoorMansChemist Cool!

[@PoorMansChemist]

@@ashe1.070 Yeah I was surprised. Figured the smell would change more than that.

[@markedis5902]

Please publish

[@öoööäoööä]

how does it smell???!!!

[@THYZOID]

it has a weird smell. nearly odorless though the smell is very faint

[@cvspvr]

like enlightenment

[@user-cd4ij4si9w]

Maybe use KBr and H2O2 more safely...

[@THYZOID]

no. there would be solubility issues. and why should i go extra steps if we can just use bromine directly? sure if your route worked it would be safer but that extra safety is not worth the extra work if you ask me

[@user-cd4ij4si9w]

@@THYZOID because I hate breathe Br². One-pot synthesis could be a very comfortable

[@mduckernz]

@@THYZOID It does work, I've tried it. If you have ready access to Br then sure, it's probably not worth it, but it is rather convenient to make it one-pot

[@eriktrp]

When da Astolfo vid coming :3

[@THYZOID]

when i get the costume :3

[@eriktrp]

@@THYZOID ThyHyZoid is real 🥳

[@brauchmernet]

TMBA anyone?

[@science_and_anonymous]

Now hydroxylate the bromide

[@kelvinpino4065]

Third comment

[@karolus28]

Cool