zinc(II) chloride T=280°C;

T=300 - 320°C;

1: With boron tribromide in dichloromethane T=-78 - 20°C; 3 h; Inert atmosphere; 2: With hydrogenchloride in dichloromethane; water T=0°C;

caesium carbonate; (η5-ethyltetramethylcyclopentadienyl)(η6-benzene)rhodium(III) hexafluorophosphate in various solvent(s) 66 h;

aluminium trichloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone in nitromethane T=25°C; 1 h;

1.1: 99 percent / H2 / Pd/C / ethanol / 1 h 2.1: NaNO2; HCl / H2O / 1 h / 0 °C 2.2: 84 percent / KI / H2O / 12 h / 25 °C 3.1: 14 percent / Cu bronze / 5 h / 250 °C 4.1: 91 percent / BBr3 / CH2Cl2 / -78 - 25 °C View Scheme

1: 14 percent / Cu bronze / 5 h / 250 °C 2: 91 percent / BBr3 / CH2Cl2 / -78 - 25 °C View Scheme

1.1: NaNO2; HCl / H2O / 1 h / 0 °C 1.2: 84 percent / KI / H2O / 12 h / 25 °C 2.1: 14 percent / Cu bronze / 5 h / 250 °C 3.1: 91 percent / BBr3 / CH2Cl2 / -78 - 25 °C View Scheme

1.1: potassium carbonate / ethanol / 16 h / Inert atmosphere; Reflux 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 43 h / Inert atmosphere; Reflux 3.1: boron tribromide / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere 3.2: 0 °C View Scheme

1.1: tetrafluoroboric acid / water / -5 °C / Inert atmosphere 1.2: 0.5 h / -5 °C / Inert atmosphere 2.1: iodine; sodium iodide / acetonitrile / 4 h / 70 °C / Inert atmosphere 3.1: potassium carbonate / ethanol / 16 h / Inert atmosphere; Reflux 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 43 h / Inert atmosphere; Reflux 5.1: boron tribromide / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere 5.2: 0 °C View Scheme