1: 63 mg / tri-n-butyltin hydride / benzene / 0.5 h / Heating; further reagents 2: 0.76 g / aluminium chloride, lithium aluminium hydride / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C 3: 2.87 g / bromine / acetic acid; acetic anhydride / 6 h 4: 268 mg / benzene / 8.5 h / Heating 5: 207 mg / N-bromosuccinimide / acetic acid / 5 h 6: 31 mg / aluminium chloride, lithium aluminium hydride / diethyl ether / 0.58 h / 20 °C View Scheme

lithium aluminium tetrahydride; aluminium trichloride in diethyl ether T=20°C; 0.583333 h;

1: 40 mg / tri-n-butyltin hydride / benzene / 4 h / Heating 2: 0.76 g / aluminium chloride, lithium aluminium hydride / tetrahydrofuran; diethyl ether / 0.33 h / 0 °C 3: 2.87 g / bromine / acetic acid; acetic anhydride / 6 h 4: 268 mg / benzene / 8.5 h / Heating 5: 207 mg / N-bromosuccinimide / acetic acid / 5 h 6: 31 mg / aluminium chloride, lithium aluminium hydride / diethyl ether / 0.58 h / 20 °C View Scheme

1: 2.87 g / bromine / acetic acid; acetic anhydride / 6 h 2: 268 mg / benzene / 8.5 h / Heating 3: 207 mg / N-bromosuccinimide / acetic acid / 5 h 4: 31 mg / aluminium chloride, lithium aluminium hydride / diethyl ether / 0.58 h / 20 °C View Scheme

1: potassium hydroxide / methanol / 2 h / Ambient temperature 2: 2.87 g / bromine / acetic acid; acetic anhydride / 6 h 3: 268 mg / benzene / 8.5 h / Heating 4: 207 mg / N-bromosuccinimide / acetic acid / 5 h 5: 31 mg / aluminium chloride, lithium aluminium hydride / diethyl ether / 0.58 h / 20 °C View Scheme

1: Heating 2: 25 mg / aluminium chloride, lithium aluminium hydride / diethyl ether / 12 h / 0 °C 3: potassium hydroxide / methanol / 2 h / Ambient temperature 4: 2.87 g / bromine / acetic acid; acetic anhydride / 6 h 5: 268 mg / benzene / 8.5 h / Heating 6: 207 mg / N-bromosuccinimide / acetic acid / 5 h 7: 31 mg / aluminium chloride, lithium aluminium hydride / diethyl ether / 0.58 h / 20 °C View Scheme

1: 25 mg / aluminium chloride, lithium aluminium hydride / diethyl ether / 12 h / 0 °C 2: potassium hydroxide / methanol / 2 h / Ambient temperature 3: 2.87 g / bromine / acetic acid; acetic anhydride / 6 h 4: 268 mg / benzene / 8.5 h / Heating 5: 207 mg / N-bromosuccinimide / acetic acid / 5 h 6: 31 mg / aluminium chloride, lithium aluminium hydride / diethyl ether / 0.58 h / 20 °C View Scheme

1: 207 mg / N-bromosuccinimide / acetic acid / 5 h 2: 31 mg / aluminium chloride, lithium aluminium hydride / diethyl ether / 0.58 h / 20 °C View Scheme

1: 268 mg / benzene / 8.5 h / Heating 2: 207 mg / N-bromosuccinimide / acetic acid / 5 h 3: 31 mg / aluminium chloride, lithium aluminium hydride / diethyl ether / 0.58 h / 20 °C View Scheme