I did a Suzuki coupling using Pd(PPh3)4 with a solvent system of 10:1 THF & water. After l-l extraction with ethyl acetate and water, the organic fraction was dried over MgSO4, reduced and fused to silica. The crude was loaded onto a silica column and purified with 7:3 EtOAc:Hex, which was alright except for some brown stuff coeluting with my product - which was probably some of the dead Pd catalyst?
I tried to redissolve my Pd-contaminated product with toluene and filter through celite, didn't work out. Also tried to remove Pd with charcoal, also didn't work out. I am one step away from ordering Pd scavenger. Could someone offer any advice on how to get rid of the brown contaminant?
Thanks in advance.