1: 1.) Br2; 2.) NaOEt / 1.) CHCl3, CCl4, -10 to 0 deg C, 1 h; 2.) CHCl3, CCl4, ethanol, 30 min 2: 77 percent / Pd(PPh3)4/NaOEt / benzene; ethanol / 2.5 h / Heating View Scheme

sodium hydroxide; iodine 1.) diethyl ether, water, 30 min; 2.) diethyl ether, water, 0 deg C, 30 min; Yield given. Multistep reaction;

bromine; sodium ethanolate 1.) CHCl3, CCl4, -10 to 0 deg C, 1 h; 2.) CHCl3, CCl4, ethanol, 30 min; Multistep reaction;