Orgopete,
I definitely agree. I pulled the procedure from the literature, and checked the phenol and allyl bromide by NMR. Both are clean. The reaction just won't go, as far as I can tell by TLC.
There is the possibility that the allyl bromide and the product move up the plates at the same rate, but that seems really doubtful. I expect the coupled product to have a higher rf value than the reactants.
I found another procedure in which Finkelstein conditions were utilized. If the way I tried doesn't work, then I suppose I will try it that way.
Thanks.