You can also have improved yields possibly by having bromobenzene 1:1 molar equiv. with the PhenylMagnesium Bromide. And byproduct only MgBr2. I would check if it is a better option. I am actually waiting on doing this synthesis for creating a compound; troparane. Using halogenated tropine to remove hydroxy and then PhenylMagnesium Bromide. - Mike
Nice reaction! Are you sure it is copper II not I chloride? I did something similar in past and protocol asked for CuCl. Also as biphenyl is ultra non polar, you can try to just stir crude solid in hexanes or heptane. It should dissolve it fully but polar stuff should stay behind. Also filtration through something like silica or alumina, not chromatography, but just filtration through like 1 cm, should clean it very well.
Yea the procedure I was following explicitly said copper(II) chloride. For purification, I was following one of the procedures from the Purification of Laboratory Chemicals encyclopedia, it does mention that passing it through alumina removes polar impurities. I've already used the biphenyl made here in another reaction which worked well, hopefully that video will be up in the coming weeks.
If I remember correctly, you need to create Grignard compount in an ice cooled enviroment or risc creating byproducts. But I could be wrong it has been an long time since I did this cond of stuff
Hello, could you give a video tutorial on the synthesis of triethylene glycol ditmethacrylate (CAS 109-16-0) and DIURETHANE DIMETHACRYLATE, MIXTURE OF ISOMERS (CAS 72869-86-4)
Is it though? The Ullmann reaction uses metallic or Cu(I) and high temperatures on aryl halides, this uses barely room temperature, Cu(II) and two grignard reagents. And it's doubtful to me that it's merely a catalytic crosscoupling either because the copper is used in stoichiometric quantity.
How are things directed with this molecule? The elecron rich nature of a second aromatic ring tells me it would be highly directing .. but things don't always behave as you expect, so I'm asking.
Electrophilic aromatic substitution (Friedel-Crafts, sulfonation, nitration, halogenation, etc.) is directed ortho and para. Though due to sterics, many reactions will only substitute the para position.
