Nice one! Looking forward to hearing how this turns out for you. Are you going the iodosafrole route to MDMA after this? My NaI arrived yesterday so I will hopefully be able to continue with my photo writeup at the weekend.  Best of luck with this anyways!

Yes, I will be performing the finkelstein reaction after this to obtain the iodo.  It will be nice having someone else to compare notes with.

Bromosafrole workup
The solution was removed from the freezer, where it had frozen (shocking).  Upon warming two layers were noticed: an upper layer which was lighter and a dark purple almost black lower layer.  Due to stirring, the salts on the bottom of the flask had taken on a purple shade as well.  The solution was decanted into a sep funnel and 2x volume of water was added.  The organic layer was drained and set aside.  The aqueous layer was then extracted twice with dichloromethane.
After extraction the organic layers had a green/gray color.

If you did your research on the reagents your using, the Glacial Acetic Acid (GAA) is acting as your solvent with a freezing point of 16.5 °C (62 °F)

Acetic acid, CH3COOH is an organic acid that gives vinegar its sour taste and pungent smell. It is a weak acid, in that it is only a partially dissociated acid in an aqueous solution. Pure, water-free acetic acid (glacial acetic acid) is a colourless liquid that absorbs water from the environment (hygroscopy), and freezes at 16.5 °C (62 °F) to a colourless crystalline solid. The pure acid and its concentrated solutions are very corrosive.

Ref: http://en.wikipedia.org/wiki/Acetic_acid

Solvent properties. Liquid acetic acid is a hydrophilic (polar) protic solvent, similar to ethanol and water. With a moderate relative static permittivity (dielectric constant) of 6.2, it can dissolve not only polar compounds such as inorganic salts and sugars, but also non-polar compounds such as oils and elements such as sulfur and iodine. It readily mixes with other polar and non-polar solvents such as water, chloroform, and hexane. With higher alkanes (starting with octane) acetic acid is not completely miscible anymore, and its miscibility continues to decline with longer n-alkanes.[11] This dissolving property and miscibility of acetic acid makes it a widely used industrial chemical.

Ref: http://en.wikipedia.org/wiki/Acetic_acid#Solvent_properties

Reaction #2
Reaction #2 was ran with similar parameters as reaction one (scale, etc) with one major change:  The flask was charged without a stirbar.  After adding the sassafras oil, the flask simply swirled a couple times and then put right in the freezer.  This was done in according to jon's original writeup which did not use stirring at all.

Comparison to Rxn 1
It was noted that the salt did not take on the purple appearance that was observed in the first reaction.  This is most likely due to the reduced interaction with the solvent.  The workup was notably different as well.

Reaction #2 workup
The reaction contents were dumped into a sep funnel and flooded with 2x volume H2O.  the mixture turned a milky orange/brown color and droplets of organic material were noted on the surface.  The sep funnel was left to sit for 10 minutes at which point there was very little separation.  Another portion of water was added, which did not help.  There was a barely perceptible organic layer on top.  ~75% of the water layer was drained, the small remaining about was extracted with DCM to yield an orang/brown organic layer, which was set aside.  The water layer was extracted twice more yielding increasing light solutions.
The organic extracts were combined and washed once with water.  This left the water looking fairly opaque.  The organic layer was then washed with sat. sodium bicard (no fizzing observed) which separated very quickly and was once again opaque.  The brine wash resulted in quick separation and a water layer that was just barely opaque.  The organic layer was now a orange/brown color, completely different from the results of the first reaction.  TLC forthcoming

I guess its hard to convey sarcasm over the internet.  The astute observer would notice that I added H2SO4 and brought it to 0C THEN added AcOH (instead of adding AcOh -> 0C -> H2SO4) because this way colligative effects will prevent the solution from freezing in an icebath.

Reaction #2
Reaction #2 was ran with similar parameters as reaction one (scale, etc) with one major change:  The flask was charged without a stirbar.  After adding the sassafras oil, the flask simply swirled a couple times and then put right in the freezer.  This was done in according to jon's original writeup which did not use stirring at all.

Procedure.

The reaction flask was charged with H2SO4 (190mmol) and chilled to 0C.  The GAA was added as such as rate that the temperature was kept below 5C. The NaBr was then added portion-wise over five minutes.  The flask took on a tangerine orange appearance.  Once the addition was complete (exothermic), the safrole was added at a rate which maintained the previous temperature.  After the addition a brown/green color was noted, along with a thin deposit of what was assumed to be NaBr on the sides of the flask. Noxious fumes were evolved, the author would suggest sniffing them to get high.  The flask was left to stir on an ice bath for 24 hours.

Ice bath = 0-1 oC

Freezer will be -20 oC or less.

jon, did you ever get a orange color like that?  I think the lack of stirring caused some problems.

I won't be able to check the TLC until monday, but I will be following DrMethoxy's suggestion of 9:1 MeOH/DMK.  Until then I used jon's H2SO4 test.  Chilled H2SO4 to 0C, then added a drop of both reaction solutions.  Both took on a deep red hue and sat on top of the H2SO4 (indicative of the product), with the second one having a noticeable purple hue (indicating presence of the alkene).  Perhaps the second had a lower percent conversion, but we won't know for sure until tomorrow.

Btw, any recommendations on what to use when staining bromosaf (if its even necessary) would be appreciated.

i don't think you will have a problem with visualization, you will need to standardize rf values.
but i researched the kinetics of this reaction.
it takes 24-30 hours to go to completion and by that i mean 93% molar yeilds.
which is'nt bad considering that the two subsequent steps are nearly quantitative.




also orange is okay bromine is darker that is what hbr looks like in solution, you guys are way overthinking this shit.

i don't think you will have a problem with visualization, you will need to standardize rf values.
but i researched the kinetics of this reaction.
it takes 24-30 hours to go to completion and by that i mean 93% molar yeilds.
which is'nt bad considering that the two subsequent steps are nearly quantitative.

Since you've research the kinetics of the Hydrohalogenation reaction of safrole + HBr, I would like to see it?

Some initial help...

Hydrohalogenation is the addition of hydrohalic acids such as HCl, HBr or HI to alkenes to yield the corresponding haloalkanes



http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/addene1.htm

http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/react2.htm

this is an exothermic reaction though, in the future i will know that cooling will accelerate things.

The rate of a reaction doubles for every 50% increase in temperature meaning there is no reaction where cooling will accelerate things baring those with a critical temperature where some other product is formed such as Li[NH₃]₄ --heat--> LiNH₂ or things like Safrol where strong acids and warm conditions will cleave the ether.