sodium hydroxide; tetrabutylammomium bromide in tetrachloromethane; water T=40°C; 1.5 h;

1: 84 percent / N-bromosuccinimide; AcOH / CHCl3 / 1 h / Heating 2: 64 percent / HCl; ZnCl2 / CCl4 / 5 h / 20 - 45 °C 3: (n-Bu)4NBr / H2O; benzene / 4 h / Heating 4: (n-Bu)4NBr; NaOH / CCl4; H2O / 1.5 h / 40 °C View Scheme

1: (n-Bu)4NBr / H2O; benzene / 4 h / Heating 2: (n-Bu)4NBr; NaOH / CCl4; H2O / 1.5 h / 40 °C View Scheme

1: 64 percent / HCl; ZnCl2 / CCl4 / 5 h / 20 - 45 °C 2: (n-Bu)4NBr / H2O; benzene / 4 h / Heating 3: (n-Bu)4NBr; NaOH / CCl4; H2O / 1.5 h / 40 °C View Scheme