1.1: HCl; NaNO2 / H2O / 0.5 h / 0 °C 1.2: 95 percent / K2CO3 / H2O; acetonitrile / 0.5 h / 0 °C 2.1: iPrMgCl*LiCl / tetrahydrofuran / 4 h / -40 - -15 °C 2.2: ZnBr2 / tetrahydrofuran / 1 h / -20 - -5 °C 2.3: 88 percent / Pd(PPh3)4 / tetrahydrofuran / 3 h / Heating 3.1: iPrMgCl*LiCl / tetrahydrofuran / 1 h / -40 °C 3.2: 75 percent / tetrahydrofuran / 2 h / 55 °C View Scheme

in tetrahydrofuran T=0°C; 0.0833333 h; Inert atmosphere; TemperatureSolvent; regioselective reaction;

in tetrahydrofuran T=-15°C; 0.333333 h; Inert atmosphere; SolventTemperature; regioselective reaction;

chloranil; xylene

carbon tetrabromide in ethanol T=24.84°C; Bromination; 30 h; Irradiation; Product distributionQuantum yield; Further Variations:Reagents;