1: 2-bromo-4-methyl-phenylamine With palladium diacetate; triphenylphosphine in tetrahydrofuran T=20°C; 0.0833333 h; 2: vinyl-magnesium bromide in tetrahydrofuran Grignard reaction; 1 h; Heating;

tetrakis(triphenylphosphine) palladium(0) in toluene T=100°C; 6 h; Inert atmosphere;

1: durch Behandlung des Diazoniumperbromids mit Alkohol 2: beim Nitrieren View Scheme

Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuBr in wss. HBr;

Na3[CuCN4]; water Diazotization;

1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane; water / 2.5 h / 80 °C / Inert atmosphere 2.1: acetic acid; sodium nitrite / water / 1.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: dichloromethane / 20 °C / Inert atmosphere 4.1: dirhodium(II) tetrakis(perfluorobutyrate) / toluene / 15 h / 90 °C / Inert atmosphere; Molecular sieve 5.1: potassium hydroxide / water / 2 h / 90 °C / Inert atmosphere 6.1: N,N-dimethyl-formamide / 15 h / 60 °C / Inert atmosphere 7.1: sodium tetrahydroborate / methanol; water / Inert atmosphere View Scheme

1.1: Et3N / tetrahydrofuran / 2 h / 0 °C 1.2: 65 percent / tetrahydrofuran / 1 h / 0 °C 2.1: MeLi / tetrahydrofuran; diethyl ether / 0 °C 2.2: t-BuLi / tetrahydrofuran; diethyl ether; heptane / 1 h / 0 °C 2.3: 72 percent / tetrahydrofuran; diethyl ether; heptane / 0.5 h / 0 °C View Scheme

1.1: 80 percent / acetic acid / 1,2-dichloro-ethane; H2O / 80 °C 2.1: phosphorus oxychloride / 0.17 h / -10 °C 2.2: 63 percent / 1,2-dichloro-ethane / 3 h / 100 °C View Scheme

acetic acid in water; 1,2-dichloro-ethane T=80°C; Paal-Knorr reaction;

sulfuric acid; sodium iodide T=0 - 140°C; 1.05 h; Schlenk technique; Overall yield = 80 percent; Overall yield = 14.3 g;