phosphorous pentoxide; sulfuric acid T=160°C; 0.5 h; Inert atmosphere;

potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); t-Bu Brett Phos; potassium bromide in 1,4-dioxane T=130°C; 16 h; Inert atmosphere;

1: in toluene T=120°C; 2: With sulfuric acid; phosphorus pentoxide Further stages.;

hydrogen bromide; copper(I) bromide; sodium nitrite in water T=0 - 75°C; Sandmeyer reaction; 12.5 h; Inert atmosphere;

1: sodium borohydride / methanol / 1 h / Ambient temperature 2: 77 percent / H2SO4 (20percent), ethylene glycol / 20 h / 75 °C View Scheme

1: sulfuric acid; potassium nitrate / 6 h / 0 - 60 °C / Inert atmosphere 2: manganese(IV) oxide / toluene / 2 h / Inert atmosphere; Reflux 3: palladium 10 on activated carbon; hydrogen / methanol / 3 h / 760.05 Torr 4: hydrogen bromide; copper(I) bromide; sodium nitrite / water / 12.5 h / 0 - 75 °C / Inert atmosphere View Scheme

1.1: N-bromosuccinmide / dichloromethane / 0.5 h / 20 °C / Inert atmosphere 1.2: 1 h / 20 °C / Inert atmosphere 2.1: sulfuric acid; potassium nitrate / 6 h / 0 - 60 °C / Inert atmosphere 3.1: manganese(IV) oxide / toluene / 2 h / Inert atmosphere; Reflux 4.1: palladium 10 on activated carbon; hydrogen / methanol / 3 h / 760.05 Torr 5.1: hydrogen bromide; copper(I) bromide; sodium nitrite / water / 12.5 h / 0 - 75 °C / Inert atmosphere View Scheme

1: palladium 10 on activated carbon; hydrogen / methanol / 3 h / 760.05 Torr 2: hydrogen bromide; copper(I) bromide; sodium nitrite / water / 12.5 h / 0 - 75 °C / Inert atmosphere View Scheme

1: manganese(IV) oxide / toluene / 2 h / Inert atmosphere; Reflux 2: palladium 10 on activated carbon; hydrogen / methanol / 3 h / 760.05 Torr 3: hydrogen bromide; copper(I) bromide; sodium nitrite / water / 12.5 h / 0 - 75 °C / Inert atmosphere View Scheme

1: 77 percent / H2SO4 (20percent), ethylene glycol / 20 h / 75 °C View Scheme