1: 80 percent / 2 h / Heating 2: 70 percent / acetone; H2O / 48 h / Ambient temperature View Scheme

With  copper; potassium carbonate; copper(I) bromide in  N,N-dimethyl-formamide 8 h;  Heating;   

Multi-step reaction with 4 steps 1: iron, acetic acid / 1 h / Heating2: acetic acid3: 92 percent / NaOCH3 / methanol / 24 h / Ambient temperature4: 91 percent / K2CO3, copper, CuBr / dimethylformamide / 8 h / Heating  

2 h;  Heating;