1: With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in ethylene glycol dimethyl ether; water Suzuki cross-coupling; 24 h; Heating; 2: With sulfuric acid 17 h; Heating; 3: With trichlorophosphate 3 h; Heating;

1.1: tetrakis(triphenylphosphine)palladium(0) / 1,2-dimethoxy-ethane / 0.5 h / 20 °C 1.2: 64 percent / Na2CO3 / 1,2-dimethoxy-ethane / 8 h / Heating 2.1: 69 percent / 20 percent H2SO4 / 3 h / Heating 3.1: NaNO2; 37 percent HCl / H2O / 1.5 h / 5 °C 3.2: 47 percent / NaN3; NaOAc / H2O / 1 h / 0 - 5 °C 4.1: 73 percent / 1,2-dichloro-benzene / 1 h / Heating View Scheme

1.1: tetrakis(triphenylphosphine)palladium(0) / 1,2-dimethoxy-ethane / 0.5 h / 20 °C 1.2: 64 percent / Na2CO3 / 1,2-dimethoxy-ethane / 8 h / Heating 2.1: 69 percent / 20 percent H2SO4 / 3 h / Heating 3.1: NaNO2; 37 percent HCl / H2O / 1.5 h / 5 °C 3.2: 47 percent / NaN3; NaOAc / H2O / 1 h / 0 - 5 °C 4.1: 73 percent / 1,2-dichloro-benzene / 1 h / Heating View Scheme

in 1,2-dichloro-benzene 1 h; Heating;

1.1: NaNO2; 37 percent HCl / H2O / 1.5 h / 5 °C 1.2: 47 percent / NaN3; NaOAc / H2O / 1 h / 0 - 5 °C 2.1: 73 percent / 1,2-dichloro-benzene / 1 h / Heating View Scheme

1.1: 69 percent / 20 percent H2SO4 / 3 h / Heating 2.1: NaNO2; 37 percent HCl / H2O / 1.5 h / 5 °C 2.2: 47 percent / NaN3; NaOAc / H2O / 1 h / 0 - 5 °C 3.1: 73 percent / 1,2-dichloro-benzene / 1 h / Heating View Scheme

in glycerol 0.25 h; Heating;