boron tribromide in dichloromethane T=-78 - 20°C;

1.1: 94 percent / Cu(NO3)2*3H2O 2.1: H2 / Raney Nickel / tetrahydrofuran; H2O / 20 °C 3.1: 92 percent / NBS / CHCl3 / 0.08 h / 20 °C 4.1: HCl; NaNO2 / tetrahydrofuran; H2O 4.2: 89 percent / urea; H3PO2 / tetrahydrofuran; H2O 5.1: 87 percent / PCC / CH2Cl2 / 0 - 20 °C 6.1: 94 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

1.1: NaNO2; aq. HCl / tetrahydrofuran / -5 °C 1.2: 87 percent / H3PO2 / 0 - 40 °C 2.1: 95 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

1.1: 90 percent / POCl3 / 60 °C 2.1: 94 percent / Cu(NO3)2*3H2O 3.1: H2 / Raney Nickel / tetrahydrofuran; H2O / 20 °C 4.1: 92 percent / NBS / CHCl3 / 0.08 h / 20 °C 5.1: HCl; NaNO2 / tetrahydrofuran; H2O 5.2: 89 percent / urea; H3PO2 / tetrahydrofuran; H2O 6.1: 87 percent / PCC / CH2Cl2 / 0 - 20 °C 7.1: 94 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

1.1: HCl; NaNO2 / tetrahydrofuran; H2O 1.2: 89 percent / urea; H3PO2 / tetrahydrofuran; H2O 2.1: 87 percent / PCC / CH2Cl2 / 0 - 20 °C 3.1: 94 percent / BBr3 / CH2Cl2 / -78 - 20 °C View Scheme

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine in ethylene glycol dimethyl ether T=120°C; Sonogashira coupling; 0.416667 h; microwave irradiation;