N-bromosuccinmide; palladium diacetate; toluene-4-sulfonic acid in 1,2-dichloro-ethane T=70°C; 12 h; Sealed tube;

1: tin; aqueous hydrochloric acid; graphite 2: Diazotization View Scheme

1: aqueous H2SO4 / Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuBr 2: tin; aqueous hydrochloric acid; graphite 3: Diazotization View Scheme

Diazotization;

1.1: isopropylmagnesium chloride / tetrahydrofuran / 3.5 h / -15 - -12 °C / Inert atmosphere 1.2: 0.5 h / -12 - 2 °C 1.3: 17 h / 55 °C 2.1: hydrogenchloride; water / acetonitrile / 50 h / 10 - 22 °C 3.1: 2,6-dimethylpyridine; pivaloyl chloride / N,N-dimethyl-formamide / 0.5 h / 5 - 10 °C / Inert atmosphere 3.2: 10 - 25 °C View Scheme

1: With potassium carbonate; N-methyl-2-(methylamino)ethylamine in N,N-dimethyl-formamide Ullmann type reaction; 0.25 h; Inert atmosphere; 2: With copper(l) iodide in N,N-dimethyl-formamide T=80°C; Ullmann type reaction; 12 h; Inert atmosphere;

sulfuric acid

1.1: isopropylmagnesium chloride / tetrahydrofuran / 3.5 h / -15 - -12 °C / Inert atmosphere 1.2: 0.5 h / -12 - 2 °C 1.3: 17 h / 55 °C 2.1: hydrogenchloride; water / acetonitrile / 50 h / 10 - 22 °C View Scheme

diethyl ether anschliessend Behandeln mit Eis und wss. HCl;