A short and efficient method was developed for the synthesis of 2-benzoxepin-3(1H)-ones. The synthetic sequence comprises of initial intermolecular Heck coupling, followed by reduction of the carbonyl functionality of the Heck product and finally base-induced intramolecular condensation. Notably, the final condensation may proceed by an interesting oxy-Michael addition, cycloreversion via double bond isomerization and intramolecular condensation.