1: 1.) HBr,Br2; 2.) NaNO2; 3.) NaOH / 1.) water, -16 deg C, 20 min; 2.) 0 deg C, 30 min; 3.) 20 deg C, 1 h 2: 27 percent / PPh3, Zn dust / Ni(PPh3)2Cl2 / dimethylformamide / 17.5 h / 50 °C View Scheme

With  sodium hydroxide; hydrogen bromide; bromine; sodium nitrite  1.) water, -16 deg C, 20 min; 2.) 0 deg C, 30 min; 3.) 20 deg C, 1 h;  Yield given. Multistep reaction;