sodium formate; N-ethyl-N,N-diisopropylamine in dimethyl sulfoxide T=90°C; 1.5 h;

in dichlorobenzene, 1,3- T=200°C; 20 h;

1.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - -2 °C 1.2: 1.67 g / K2CO3 / acetonitrile; H2O / 0 - 20 °C 2.1: PdCl2(P(C6H5)3)2; CuI; triethylamine / 50 °C 3.1: 170 mg / K2CO3 / tetrahydrofuran; methanol / 4 h / 20 °C 4.1: 96 percent / 1,2-dichloro-benzene / 200 °C View Scheme

1.1: (C6H5CH2)(CH3)3N(1+)*Cl(1-); CaCO3 / CH2Cl2; methanol / 24 h 2.1: HCl; NaNO2 / acetonitrile; H2O / 0.5 h / -5 - -2 °C 2.2: 1.67 g / K2CO3 / acetonitrile; H2O / 0 - 20 °C 3.1: PdCl2(P(C6H5)3)2; CuI; triethylamine / 50 °C 4.1: 170 mg / K2CO3 / tetrahydrofuran; methanol / 4 h / 20 °C 5.1: 96 percent / 1,2-dichloro-benzene / 200 °C View Scheme