Journal of the Chemical Society, Chemical Communications

Me2C:NOH reacted with the Cr(CO)3-complexed haloarenes I (R = H, 2-, 3-, 4-Me, R1 = F; R = 2-OMe, 2-Me, R1 = Cl) under solid-liq. phase transfer conditions to give 75-98% complexed O-aryloximes I (R as before, R1 = ON:CMe2) (II). Decomplexation of II with iodine gave 55-81% RC6H4ONCMe2 (III; R as before). Cyclization of III (R = 2-, 3-, 4-Me, 2- OMe) in refluxing EtOH-H2SO4 gave 45-87% benzofuran IV (R = 4-, 5-, 6-, 7-Me, 4-, 6-OMe).