triethylsilane; boron trifluoride diethyl etherate in dichloromethane T=0°C; 0.5 h;

1: pyridine / 17 h / Ambient temperature 2: 86 percent / thionyl chloride / pyridine / 19 h / 0 °C 3: 4 percent / manganese(III) acetate dihydrate, acetic anhydride / acetic acid / 10 h / Heating View Scheme

phosphorus tribromide in benzene

sodium azide; iodobenzene dichloride in ethyl acetate T=0 - 80°C; Curtius Rearrangement; 12 h; Inert atmosphere;

With  lithium aluminium tetrahydride in  tetrahydrofuran