1.1: conc. HCl; sodium nitrite / H2O / 0.5 h / 0 °C 1.2: 92 percent / potassium carbonate / H2O; acetonitrile / 0 - 20 °C 2.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 2.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 2.3: 78 percent / Pd(PPh3)4 / tetrahydrofuran / Heating 3.1: 95 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C View Scheme

1.1: i-PrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 1.2: ZnBr2 / tetrahydrofuran / 1 h / -40 - -5 °C 1.3: 78 percent / Pd(PPh3)4 / tetrahydrofuran / Heating 2.1: 95 percent / potassium hydrogen sulfate; sodium azide / CH2Cl2; H2O / 12 h / 20 °C View Scheme

in 1,3,5-trimethyl-benzene 5 h; Heating;

in N-dodecane T=180 - 200°C;