Multi-step reaction with 7 steps 1: 94 percent / imidazole, 1-hydroxybenzotriazole / dimethylformamide / 72 h / 50 - 60 °C2: 1.) NBS; 2.) γ-collidine / 1.) hexane, reflux, 1 h; 2.) xylene, reflux, 1 h3: 64 percent / dimethylsulfoxide; tetrahydrofuran / Ambient temperature4: 1.) 9-BBN; 2.) NaOH, H2O2 / 1.) THF, r.t., 16 h5: 1.) NaH; 2.) O2, PdCl2, CuCl / 1.) xylene, reflux, 18 h; 2.) DMF-H2O, r.t. 19 h6: 79 percent / tetrahydrofuran / 1 h / 0 °C  

Multi-step reaction with 6 steps 1: 1.) NBS; 2.) γ-collidine / 1.) hexane, reflux, 1 h; 2.) xylene, reflux, 1 h2: 64 percent / dimethylsulfoxide; tetrahydrofuran / Ambient temperature3: 1.) 9-BBN; 2.) NaOH, H2O2 / 1.) THF, r.t., 16 h4: 1.) NaH; 2.) O2, PdCl2, CuCl / 1.) xylene, reflux, 18 h; 2.) DMF-H2O, r.t. 19 h5: 79 percent / tetrahydrofuran / 1 h / 0 °C  

Multi-step reaction with 5 steps 1: 64 percent / dimethylsulfoxide; tetrahydrofuran / Ambient temperature2: 1.) 9-BBN; 2.) NaOH, H2O2 / 1.) THF, r.t., 16 h3: 1.) NaH; 2.) O2, PdCl2, CuCl / 1.) xylene, reflux, 18 h; 2.) DMF-H2O, r.t. 19 h4: 79 percent / tetrahydrofuran / 1 h / 0 °C  

Multi-step reaction with 4 steps 1: 1.) 9-BBN; 2.) NaOH, H2O2 / 1.) THF, r.t., 16 h2: 1.) NaH; 2.) O2, PdCl2, CuCl / 1.) xylene, reflux, 18 h; 2.) DMF-H2O, r.t. 19 h3: 79 percent / tetrahydrofuran / 1 h / 0 °C