1: m-C6H4BrBCl2 With i -Pr2Zn in diethyl ether T=25°C; 2 h; 2: in tetrahydrofuran T=-30°C; 0.166667 h; 3: propargyl bromide in tetrahydrofuran T=20°C; Further stages.;

tetrakis(triphenylphosphine) palladium(0); sodium methylate in N,N-dimethyl-formamide T=20°C; Suzuki-Miyaura cross coupling reaction; 3 h; Inert atmosphere;

chromium hexacarbonyl in dimethyl sulfoxide T=130°C; Inert atmosphere;

1.1: BCl3 / CH2Cl2 / 10 h / 25 °C 2.1: Br2 / 16 h / 25 °C 3.1: i-Pr2Zn / diethyl ether / 2 h / 25 °C 3.2: CuCN*2LiCl / tetrahydrofuran / 0.17 h / -30 °C 3.3: 46 percent / tetrahydrofuran / 20 °C View Scheme

1.1: Br2 / 16 h / 25 °C 2.1: i-Pr2Zn / diethyl ether / 2 h / 25 °C 2.2: CuCN*2LiCl / tetrahydrofuran / 0.17 h / -30 °C 2.3: 46 percent / tetrahydrofuran / 20 °C View Scheme