1: 1.) Br2, 2.) silver fluoride / 1.) CCl4, RT, 1 h, 2.) THF, H2O, 30 min 2: p-toluenesulfonic acid / 15 h / Heating 3: 1.) Mg, ethylene dibromide, 2.) B2H6, 3.) aq. NaOH, H2O2 4: NaBH4 / ethanol / 0.5 h 5: p-toluenesulfonic acid / benzene / 1 h / Heating 6: pyridine / 3 h 7: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / Heating 8: K2CO3 / methanol; tetrahydrofuran / 0.5 h / 0 °C View Scheme

Multi-step reaction with 2 steps 1: 1.) Br2, 2.) silver fluoride / 1.) CCl4, RT, 1 h, 2.) THF, H2O, 30 min2: p-toluenesulfonic acid / 15 h / Heating  

Multi-step reaction with 6 steps 1: 1.) Br2, 2.) silver fluoride / 1.) CCl4, RT, 1 h, 2.) THF, H2O, 30 min2: p-toluenesulfonic acid / 15 h / Heating3: 1.) Mg, ethylene dibromide, 2.) B2H6, 3.) aq. NaOH, H2O2 4: NaBH4 / ethanol / 0.5 h5: p-toluenesulfonic acid / benzene / 1 h / Heating6: pyridine / 3 h  

Multi-step reaction with 4 steps 1: 1.) Br2, 2.) silver fluoride / 1.) CCl4, RT, 1 h, 2.) THF, H2O, 30 min2: p-toluenesulfonic acid / 15 h / Heating3: 1.) Mg, ethylene dibromide, 2.) B2H6, 3.) aq. NaOH, H2O2 4: NaBH4 / ethanol / 0.5 h