1: 64 percent / dimethylsulfoxide; tetrahydrofuran / Ambient temperature 2: 1.) 9-BBN; 2.) NaOH, H2O2 / 1.) THF, r.t., 16 h 3: 86 percent / NaH / xylene / 22 h / Heating View Scheme

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 2 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 h  

With  2,4,6-trimethyl-pyridine; N-bromosuccinmide  1.) hexane, reflux, 1 h; 2.) xylene, reflux, 1 h;  Yield given. Multistep reaction;   

Multi-step reaction with 3 steps 1: 64 percent / dimethylsulfoxide; tetrahydrofuran / Ambient temperature2: 1.) 9-BBN; 2.) NaOH, H2O2 / 1.) THF, r.t., 16 h3: 86 percent / NaH / xylene / 22 h / Heating