1: 86 percent / Zn(Hg), 9 M aq. HCl, glacial acetic acid / toluene / 48 h / Heating 2: 1.) H2SO4, 2.) Br2 / 1.) reflux, 24 h, 2.) CCl4 View Scheme

1: 70 percent / AlCl3 / nitrobenzene / 25 °C 2: 86 percent / Zn(Hg), 9 M aq. HCl, glacial acetic acid / toluene / 48 h / Heating 3: 1.) H2SO4, 2.) Br2 / 1.) reflux, 24 h, 2.) CCl4 View Scheme

1: 70 percent / AlCl3 / nitrobenzene / 25 °C 2: 86 percent / Zn(Hg), 9 M aq. HCl, glacial acetic acid / toluene / 48 h / Heating 3: 1.) H2SO4, 2.) Br2 / 1.) reflux, 24 h, 2.) CCl4 View Scheme

sulfuric acid; bromine 1.) reflux, 24 h, 2.) CCl4; Yield given. Multistep reaction;