iodine; potassium carbonate in methanol 1.) r.t., 2 h, 2.) 0 deg C, overnight;

1: (i-Pr)2NEt / toluene / 0 °C 2: 1 h / 0 °C 3: 85 percent / K2CO3, I2 / methanol / 1.) r.t., 2 h, 2.) 0 deg C, overnight View Scheme

1: KOH / methanol / 2 h / Heating 2: (i-Pr)2NEt / toluene / 0 °C 3: 1 h / 0 °C 4: 85 percent / K2CO3, I2 / methanol / 1.) r.t., 2 h, 2.) 0 deg C, overnight View Scheme

1: 1.) SOCl2, pyridine / 1.) C6H6, r.t., 1 h, 2.) reflux, overnight 2: KOH / methanol / 2 h / Heating 3: (i-Pr)2NEt / toluene / 0 °C 4: 1 h / 0 °C 5: 85 percent / K2CO3, I2 / methanol / 1.) r.t., 2 h, 2.) 0 deg C, overnight View Scheme

in acetonitrile; benzene 6 h; Irradiation;

6 h; Irradiation;