1: 78 percent / Br2, dioxane / diethyl ether / 0.5 h 2: K, NH3(liquid), Fe(NO3)3 / 3 h 3: 1.) HNO2, 2.) Cu2(CN)2, NaCN / 1.) 0 deg C, 2.) a) H2O, toluene, 0 deg C, 30 min, b) 60 deg C, 1 h 4: 70 percent / 90percent formic acid / Raney Ni / H2O / 6 h / Heating View Scheme

1: 78 percent / Br2, dioxane / diethyl ether / 0.5 h 2: K, NH3(liquid), Fe(NO3)3 / 3 h 3: 1.) HNO2, 2.) Cu2(CN)2, NaCN / 1.) 0 deg C, 2.) a) H2O, toluene, 0 deg C, 30 min, b) 60 deg C, 1 h 4: 70 percent / 90percent formic acid / Raney Ni / H2O / 6 h / Heating 5: t-BuOK / 2-methyl-propan-2-ol; dimethylsulfoxide / 1.5 h / 55 - 60 °C 6: NaOMe / ethanol / 24 h / Heating View Scheme

2: 89 percent / boron tribromide-methylsulfide / 1,2-dichloro-ethane / 24 h / Heating View Scheme