chloro-trimethyl-silane; sodium iodide in acetonitrile T=60°C; 3 h;

boron tribromide in dichloromethane 15 h; Heating;

1.1: K2CO3 / acetone / 2 h / Heating 1.2: 92 percent / acetone / 3 h / Heating 2.1: Mg / diethyl ether / 0.5 h / 20 °C 2.2: diethyl ether / 3 h / Heating 2.3: 88 percent / aq. HCl 3.1: 85 percent / 4-chloroanil / benzene / 5 h / Heating 4.1: 82 percent / trimethylsilyl chloride; NaI / acetonitrile / 3 h / 60 °C View Scheme

1.1: Mg / diethyl ether / 0.5 h / 20 °C 1.2: diethyl ether / 3 h / Heating 1.3: 88 percent / aq. HCl 2.1: 85 percent / 4-chloroanil / benzene / 5 h / Heating 3.1: 82 percent / trimethylsilyl chloride; NaI / acetonitrile / 3 h / 60 °C View Scheme

1: 85 percent / 4-chloroanil / benzene / 5 h / Heating 2: 82 percent / trimethylsilyl chloride; NaI / acetonitrile / 3 h / 60 °C View Scheme

1: 1.) Mg; 3.) H2SO4 (1N) / 1.) Et2O, reflux, r.t., 1 h; 2.) Et2O, reflux, 3 h 2: 74 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 5 h / Heating 3: 63 percent / 1.0M Br3B / CH2Cl2 / 15 h / Heating View Scheme