triethylamine in dichloromethane T=0°C; 2 h; Yield given;

1: 59 percent / CH2Cl2 / 24 h / 20 °C 2: 70 percent / SOCl2 / toluene / 48 h / 20 °C View Scheme

Nafion-H in benzene 0.25 h; Heating;

1: pyridine / 1.5 h / Heating 2: 57 percent / bromine / CCl4 / 1 h / Irradiation 3: 80 percent / H2O; acetone / 3 h / Heating View Scheme

1: PdCl2(MeCN)2 / tetrahydrofuran / 16 h / Ambient temperature 2: NaH / 1,2-dimethoxy-ethane / 4 h / Heating 3: 72 percent / 2-methyl-propan-2-ol / 15 h / Heating 4: 97 percent / HCl gas / methanol / 0.25 h 5: 1.) conc. HCl, 2.) NaNO2 / 1.) EtOH, H2O, 50 deg C, 2.) EtOH, H2O, 10 deg C, 15 min View Scheme

dichloro bis(acetonitrile) palladium(II) in tetrahydrofuran 16 h; Ambient temperature;

in tetrahydrofuran T=-78 - 20°C; 8 h;

dichloro bis(acetonitrile) palladium(II) in tetrahydrofuran 16 h; Ambient temperature;