In this paper, the synthesis of 3-aryl-2,5-dihydro-1-benzoxepines is described. While the reaction was started from phenol and based on the sequential reactions such as Claisen rearrangement, O-alkylation, Wittig reaction, and ring-closing metathesis (RCM), a series of new 3-aryl-1-benzoxepines were prepared in good overall yields.