Stability Condition To Avoid: DECOMPOSES ON EXPOSURE TO LIGHT.
Is there a way to use this for a grignard without distilling. It seems swigs only problem is un-reacted benzyl alcohol, which has active hydrogen’s.
That's very simplistic. You know bromine is an oxidizer, right? It's very likely that benzaldehyde has formed, and maybe benzoic acid, and hence also benzyl benzoate by simple esterification. Not to mention benzal bromide (which is likely to polymerize upon addition of Mg...
So are you saying that Swig should be ok with ~198°C?
Yes - just avoid strong illumination.
Hmmm, SWIM didn't know that then. SWIM distilled right in front of a window during the day dammnit! Maybe weird gak formations and color changes in the still flask will be way less if done in a darker setting, probably giving higher yeilds.
SWIM still sticks with his original opinion in the original thread you started. If your gonna fuck with benzyl halides at all, just use the chloride. Like Rhodium had said it's cheaper, easier, and way less messy. SWIM can also "back that up" from personal experience.
Hey Rhodium:
A halide swap will work for a benzyl halide right?
Amalgam, did you use Al foil to contain the heat, what oil was used, did you do a reaction with the benzyl bromide?
When SWIM gently refluxed the crudely distilled Br2 with the toluene, or during workup distillation? Either way...no.
What oil did I use? If you mean for a heating bath, none. SWIM used a controlled mantle. It's an old ass Glass-Col.
Rhodium, From everything that swig has read, benzyl bromide is better, and benzyl iodine is even better. Would you go the chloride route or bromide, if you had HBr around.
That all depends. SWIM cannot get benzyl alcohol in heaping quantities without ordering it from a supplier, which is something SWIM won't do seeing as the end product that'll be made is very illegal and any attention from any supplier is unwanted to SWIM. SWIM always works 100%otc. So toluene is something SWIM will start from.
But even if SWIM had HBr (wich SWIM can make very easily anyway) and benzyl alcohol, SWIM would save that HBr for something else. Muriatic is very cheap to get, just heat the muriatic and the alcohol with lewis acid catalyst to get the chloride. Separate and distill organics obtaining the chloride.
If benzyl bromide or even the iodide is what you wanted, you could do the halide swap. The chloride is just as easy to make and is cheaper in the long run. KI is cheaply available from those local photoshop chemistry stores by the pound (also very cheap). Dilute the chloride in acetone and add the KI and reflux. Filter precipitated KCl and distill off the acetone (recycling it for another run perhaps). Viola, benzyl iodide that after some extra drying will probably run perfectly in a grignard. One thing SWIM has noticed is that when trying to distill the bromide (and probably more so with the iodide) the polymerization gak thing happens in the still flask, but has never seen it with the chloride, as it's bp is lower anyway. Once one has pure chloride the halide swap will give the iodide (or the bromide) without the need to distill it, probably with higher yeilds to. There's probably a high loss involved when distilling the bromide (as indicated somewhat by SWIMS past experiments to).
Also, to answer your question about using the bromide SWIM had made in a reaction.....no, not the bromide. SWIM never made enough and was just tinkering around with the idea anyway, never intended to even get this serious with the bromide. When SWIM did it, it seemed like too much trouble to go through, cause you have to remember SWIM made his own bromine from KBr, H2SO4 and H2O2 (a rather sucky way I might add), distilled it then added to toluene and refluxed. The shit brought me to my knees in tears from even just trying to clean my glassware, and the gak shit in the still flask seemed troublesome and was hard to clean, so SWIM left it alone and made the chloride.
SWIM has made the chloride and used it however, to react with alcoholic cyanide solution to make the nitrile, which reacted with 70%H2SO4 to give PAA without a hitch. SWIM used the PAA to make you know what.
P.S. Rhodium have you ever messed with benzyl chloride, is it much less of a lachamayor then benzyl bromide?
YES!