1: 75 percent / N-bromosuccinimide, dibenzoylperoxide / CCl4 / 6 h / Heating 2: 1.) sodium borohydride, diphenyl diselenide; 2.) 30percent H2O2 / 1.) ethanol, THF, 2.5 h, reflux; 2.) THF, ethanol, 3 h, 0 deg C View Scheme

Multi-step reaction with 3 steps 1: 77 percent / K2CO3, potassium tert-butoxide / dimethylformamide; tetrahydrofuran / Ambient temperature2: 88 percent / sodium acetate, H2 / 10percent Pd/C / benzene; acetic anhydride / 24 h3: 65 percent / pyridine / 12 h  

Multi-step reaction with 4 steps 1: 93 percent / sodium dithionite / H2O; dioxane / 0.5 h / Ambient temperature2: 77 percent / K2CO3, potassium tert-butoxide / dimethylformamide; tetrahydrofuran / Ambient temperature3: 88 percent / sodium acetate, H2 / 10percent Pd/C / benzene; acetic anhydride / 24 h4: 65 percent / pyridine / 12 h  

Multi-step reaction with 11 steps 1: 1.) nBuLi / 1.) THF, r.t.; 2.) r.t.2: 87 percent / 25percent HCl / Heating3: 92 percent / acetone / Ambient temperature4: 97 percent / N-bromosuccinimide / dimethylformamide / Ambient temperature5: 1.) NaNO2, 20percent HCl / 1.) 0 deg C; 2.) H2O, 65 deg C6: 91 percent / tetrahydrofuran / Ambient temperature7: 1.) 49percent HF; 2.) MnO2 / 1.) THF, r.t.; 2.) CH2Cl2, reflux8: pyridine, 4-dimethylaminopyridine / ethyl acetate / Ambient temperature9: 97 percent / tetrahydrofuran / Ambient temperature10: 1.) zinc, acetic acid / 1.) 80 deg C; 2.) Me2CO, r.t.11: 44 percent / tetrakis(triphenylphosphine)palladium  

With  N-bromosuccinmide; dibenzoyl peroxide in  tetrachloromethane 6 h;  Heating;   

With  N-bromosuccinmide; dibenzoyl peroxide in  tetrachloromethane 8 h;  Heating;