[yetyet]

Hi, I am an undergraduate student conducting research on Suzuki-Miyaura polymerization.

After synthesizing the monomer by in-situ trapping, which is OHex, B(OH)₂ and Br to the benzene ring. I have trouble in isolating the product as I can't fully extract the product using organic solvent from the mixture as I can always detect somthing (assuming the product since it is a boronic acid) on TLC plate. I tried Et₂O and AcOEt but I still have the same problem.

If anyone have any idea how with this, it would help me a lot. Thank you!

[rolnor]

I dont understand what compound you are making. It sounds like an interesting project. Do you have a reference you are using, a paper? To isolate boronic acids can probably be a bit tricky, boron is different and can behave strangely.

[yetyet]

Thank you for replying rolnor.

The reference that i was using is https://doi.org/10.1021/ol015598+

The functional group here is OHex and with Bromine at the para-position. However, instead of working up with neopentyl glycol, I used HCl to convert it to Boronic Acid.

This reaction should worked because after reaction with neopentyl glycol I got a very good yield. So my only problem is isolating the Aryl Boronic Acid that i just synthesized.

[rolnor]

To mix this with HCl can give you a mess, why dont you use the boronic-ester? Try to follow the procedure you have is my tip. The OHex is a weak activating group and lithiation might be slow at -78, I have used OMe and in that case I used 0 degrees Celsius and BuLi for ortho-lithiation