dihydrogen peroxide; tetra-(n-butyl)ammonium iodide in water T=20°C; chemoselective reaction;

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: 116 mg / 2M-aq. sodium hydroxide / dioxane / 2.75 h View Scheme

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: 116 mg / 2M-aq. sodium hydroxide / dioxane / 2.75 h View Scheme

1: 2.87 g / bromine / acetic acid; acetic anhydride / 6 h 2: 116 mg / 2M-aq. sodium hydroxide / dioxane / 2.75 h View Scheme

1: potassium hydroxide / methanol / 2 h / Ambient temperature 2: 2.87 g / bromine / acetic acid; acetic anhydride / 6 h 3: 116 mg / 2M-aq. sodium hydroxide / dioxane / 2.75 h 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: 116 mg / 2M-aq. sodium hydroxide / dioxane / 2.75 h 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: 116 mg / 2M-aq. sodium hydroxide / dioxane / 2.75 h View Scheme

sodium hydroxide in 1,4-dioxane 2.75 h;

hydrogenchloride in 1,4-dioxane 0.666667 h; Heating;