After N-chlorobenzanilide (1) was had stood in ether solution containing iron (III) chloride-hydrogen chloride complex (FeCl3-HCl) at room temperature, 2-chloro and 4-chlorobenzanilides were obtained as the rearrangement products. Remarkable differences in reaction rates and product distribution were noted for the Orton rearrangenment of 4'-methylbenzanilide (2), 4', N-dichlorobenzanilide (3) and 4'-nitrobenzanilide (4) using FeCl3-HCl. The order of the reaction rates was as follows; 4>2>1>3, the yields of rearrangement products; 2>1>3>4, and yields of dechloronated products; 4>3>2=1=0. Reaction of 1 with iron (III) bromide-hydrogen bromide complex (FeBr3-HCl) gave 4-bromobenzanilide as the sole product. The Orton rearrangement of 1 apparently proceeds via an intermolecular pathway in para-position, while ortho-chlorination of 1 may occure via both inter- and intramolecular pathways.