triphenylphosphine; zinc; NiCl2((PPh3)P)2 in N,N-dimethyl-formamide T=50°C; 17.5 h;

tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=120°C; 60 h;

Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran / -95 - -90 °C1.2: I2 / tetrahydrofuran2.1: 80 percent / LDA / tetrahydrofuran / -85 °C3.1: 70 percent / Pd(PPh3)4 / tetrahydrofuran / 0 °C  

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;