The alkylation of bromobenzene with allyl acetate on zeolite H-USY (Si/Al 30) was studied in liquid phase conditions, at 150 °C. Reactions were performed at different space velocities (LHSV = 60, 120, 240 and 480 h-1) in tubular plug flow reactors using a high-throughput frontal analysis setup. Besides the desired alkylation products, cis-propenyl bromobenzene (cis-PBB) and trans-propenyl bromobenzene (trans-PBB) and a dialkylated product, light and heavy side products were formed. Polymerization reactions starting from allyl acetate lead to blocking of the zeolite pores, and result in catalyst deactivation. Based on the experimental data, several molecular kinetic models were proposed, and implemented in a reactor model, accounting for axial dispersion, mass transfer into the catalyst crystals, competitive adsorption effects and catalyst deactivation. Model discrimination revealed the underlying reaction mechanisms.