A polyurethane prepared from 1,9-nonanediol and toluene-2,4-diisocyanate with Mn=11,840, was capped on both ends in a reaction with 4-(benzocyclobutenyl) methanol. The polyurethane was used to crosslink styrene-butadiene rubber through Diels-Alder reactions on the benzocyclobutene functionality. The synthesis and characterization of 4-(benzocyclobutenyl) methanol, a molecule not reported previously, is presented. The crosslinking reaction was carried out on intimate mixtures of the telechelic polyurethane and SBR at elevated temperature and pressure. Various physical properties of the crosslinked material were studied.