Natural Science Forum / Chemistry / Organic Synthesis / March 2007

I am trying to brominate an ortho-allyl bisphenol at the allylic
position. I have tried 2 eq of NBS in CCl4 at reflux using either
incandenscent light or benzoyl peroxide as an initiator. the reactions
were performed under an argon atmosphere. The reaction seems to have
worked, based on the presence of succinimide at the top of the
reaction, but I am having trouble in the workup. The TLC is a long
smear, presumably an acid flame from HBr. My workup has been wash once
with saturated bicarb, then twice with h2o. I then did quick
purification on silica. However, I am expecting a solid and have
gotten an oil. Does anyone have any advice on how to workup these
reactions or purify them. Thanks for your help.