1.1: hydrogen; palladium 10 on activated carbon; triethylamine / 6225.62 Torr 2.1: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 3.1: hydrogenchloride / methanol / 3 h / 20 °C / |Reflux 4.1: N,N,N',N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / |Inert atmosphere 4.2: 2 h / -10 - 0 °C 5.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 5.2: 2 h / 50 °C View Scheme

1.1: toluene-4-sulfonic acid / methanol / 0.58 h 2.1: hydrogen; palladium 10 on activated carbon; triethylamine / 6225.62 Torr 3.1: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 4.1: hydrogenchloride / methanol / 3 h / 20 °C / |Reflux 5.1: N,N,N',N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / |Inert atmosphere 5.2: 2 h / -10 - 0 °C 6.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 6.2: 2 h / 50 °C View Scheme

1.1: sodium hydroxide; bromine / water; 1,4-dioxane / 3 h / 5 - 7 °C 2.1: hydrogenchloride / methanol / 3 h / 20 °C / |Reflux 3.1: N,N,N',N,-tetramethylethylenediamine; chloro-trimethyl-silane / dichloromethane / 0.5 h / -10 °C / |Inert atmosphere 3.2: 2 h / -10 - 0 °C 4.1: potassium tert-butylate / N,N-dimethyl-formamide / 1.33 h / -15 °C 4.2: 2 h / 50 °C View Scheme

potassium hydroxide 4 h; Heating; Title compound not separated from byproducts;

1: 95 percent / tetrahydrofuran / 18 h / 22 °C 2: tetrahydrofuran / 18 h / Heating View Scheme