Btw, would it be possible to directly gas the safrole/allylbenze with gaseus HBr, instead of using 62% aqueus HBr or the 40% HBr in glacial acdtic acid?

Yes you can but you must use a solvent that dissolves HBr such as acetic acid.

@ jon : I am sorry, i wouldn't say you're a faker but all your reports are not complete. You porbably know that chemistry is a precise science and all the measures MUST be noted and explain. You wrote "HBr 40%" but you didn't talk about the solvent. For me when you say HBr 40% , that means it's dissolved into water if you don't precise the solvent. If you write "HBr 33%" i'll gess it's HBr in AcOH but writing all the information don't cost anything... Image all the people who tried this reaction with 40% aqueous HBr Next time, be precise please.

Thank you.

Dr.MeO

Has anyone ever attempted the hydrobromination of an alkene using Glycolic acid or Glyoxylic acid as the solvent for the HBr instead of AcOH.

I looking for a solvent that can be had easier then AcOH. I know no synthesis or over the counter sources for sodium propanate either. Wht other suggestions do you folks have for performing this reaction in that can be had quickly on the cheep. Don't say DMSO because I don't really believe it  when people say I works for this reaction.

I dont give a fuck who calls me or what ever I just want to synthesis it. End of stopry .. Stop tryingto get me to order shiit I do that when I feel the need. Kapesh!

Can someone kindly do a little write-up of this procedure? I can't make sense of Jon's non-punctuational rambling, but do feel there is substance hidden in the gobbledygook.

Can someone kindly do a little write-up of this procedure? I can't make sense of Jon's non-punctuational rambling, but do feel there is substance hidden in the gobbledygook.

It took several hours of reformatting to make that old Hive thread able to be posted in this one, all the information that one skilled in the art of organic chemistry would need is already in this thread  If you can't figure it out that's your problem    The result comes from the effort applied 

I tihink you misunderstood me. I am not seeking a write-up a la Bright-Star, but rather a cogent explanation of the procedure. I am well aware and am familiar with bromination of alkenes as well as the Finkelstein reaction which all minds seem to arrive on a particularly useful switcheroo to form iodosafrole.

I was look more for reaction parameters used that would lead to success. I'm not a newb by any means.

Lest you all forget, the tiltle of this very thread is a complaint about Jon's vague ramblings and the OPs subsequent inability to result in bromosafrole. Its one thing to say, throw some sodium bromide in them that tubs along wit some H2So4 and some Glacial Acetic and your all good, versus a cogent discussion about the parameters of the reaction and reactants.

Sorry if I come off whiny. Its just I'm particularly excited about this route.

You sir have a point. Chemistry is about reproducibility of one`s results. If it aint reproducible, it aint worth shit.

Now there we go! No need for dimensional analyses, but considering that you mention yield is highly dependent on workup, what is your preferred method of workup?

Thanks for indulging me, Jon!

Most people use an acid base extraction and/or fractional vacuum distillation to purify their work, it's doubtful that jon does things very differently but maybe he'll humor you with his version of what can be found all over the internet  LT/ describes a work up in this thread, maybe you should try reading what's been posted already  This site doesn't want exact Betty Crocker recipes posted, it's mostly for those skilled in the art 

it's very simple once the bromsafrole has reacted it's taken from the freezer and the liquid phase is slowly decanted from the salts.
this takes time so patience is key.
the salts are dissolved fully in water and extracted with any chlorinated hydrocarbon does'nt matter it could be tce.
extracted only once the phases separated and the aqueous dumped.
the acid is diluted with 1-2 volumes of water you don't have to be exact.
you'll see phase separation now pour into sep funnel and separate phases.
use the same solvent from the previous extration and extract the aqueous phase.
separate and extract the aqueous once more this time with less solvent maybe 1/2 maybe 1/3 look for color change see if the solvent takes on a green or burgandy hue if it does'nt you can combine it with the bromsafrole or you can dump it along with the acid it's up to the chemist.
now to the bromosafrole and solvent pour into sep funnel add equal volume water and start adding bicarb and swirl do this carefully watch for fizzing add bicarb until the fizzing stops.
separate the bottom layer and discard the top layer aqueous layer.
wash once again with water, then brine then take the solvent off under a vacum (for heavier chlorinated hydrocarbons use a hot water bath)
whalla bromosafrole.
when i talk about workup you have to be mindful of mechanical loss spills, product clinging to glass. etc.
 this one will get you; all the safrole derivatives: mdp2p, md2brpropane, and safrole are all volatile, for example you could have some sitting in a beaker come back 8 hours later and 1/3 of it is gone, because it is volatile.
just little stuff like this can be the inspiration for new curse words to be invented.
 re: distillation
 bolloks! it is bad practice in general to distill high boiling organic halides bromides and iodides tend to decompose on heating to tar and polymeric gunk.