1: 68 percent / 1.) Br / 2.) THF, 2.) 25 deg C, 30 min 2: 73 percent / NaBH4 / methanol / 0.5 h / 25 °C 3: pyridine; diethyl ether / 6 h / Heating 4: 5.84 g / NaBr / dimethylformamide / 5 h / 50 °C 5: 5.8 g / 1.) n-BuLi, TMEDA / 1.) THF, 2.) -15 deg C, 1 h; 20 deg C, 2 h 6: 77 percent / H2SO4 conc. / 4 h / Heating 7: 1.64 g / 1.) n-BuLi / 1.) Et2O, reflux, 1 h, 2.) THF 8: 0.21 g / LiOH / H2O / 8 h / 25 °C / electrochemical reduction 9: diethyl ether / 0.5 h / 0 °C 10: m-CPBA / CH2Cl2 / 12 h / 0 °C View Scheme

1: 60 percent / dimethylsulfoxide 2: 67 percent / KOH / ethane-1,2-diol; H2O; ethanol / 18 h / Heating 3: 86 percent / oxalyl chloride, pyridine / benzene / 2 h / Ambient temperature 4: 76 percent / triethyl amine / diethyl ether / 1 h / Ambient temperature 5: 82 percent / diethyl ether / Ambient temperature 6: 38 percent / acetonitrile / Irradiation View Scheme

1: 60 percent / dimethylsulfoxide 2: 67 percent / KOH / ethane-1,2-diol; H2O; ethanol / 18 h / Heating 3: 86 percent / oxalyl chloride, pyridine / benzene / 2 h / Ambient temperature 4: 76 percent / triethyl amine / diethyl ether / 1 h / Ambient temperature 5: 82 percent / diethyl ether / Ambient temperature 6: 17 percent / acetonitrile / Irradiation View Scheme

1: 60 percent / dimethylsulfoxide 2: 67 percent / KOH / ethane-1,2-diol; H2O; ethanol / 18 h / Heating 3: 86 percent / oxalyl chloride, pyridine / benzene / 2 h / Ambient temperature 4: 76 percent / triethyl amine / diethyl ether / 1 h / Ambient temperature 5: 82 percent / diethyl ether / Ambient temperature 6: 17 percent / acetonitrile / Irradiation View Scheme

1: 60 percent / dimethylsulfoxide 2: 67 percent / KOH / ethane-1,2-diol; H2O; ethanol / 18 h / Heating 3: 86 percent / oxalyl chloride, pyridine / benzene / 2 h / Ambient temperature 4: 76 percent / triethyl amine / diethyl ether / 1 h / Ambient temperature 5: 82 percent / diethyl ether / Ambient temperature 6: 17 percent / acetonitrile / Irradiation View Scheme

bromine 2.) THF, 2.) 25 deg C, 30 min;

Montmorillonite K-10 clay T=200°C; Friedel-Crafts alkylation; 5 h;

pyridine; phosphorus tribromide in diethyl ether T=0 - 20°C; 3 h;

1: 93 percent / NaBH4/Al2O3 / 0.02 h / microwave irradiation 2: 73 percent / PBr3; pyridine / diethyl ether / 3 h / 0 - 20 °C View Scheme

tri-n-butylhexadecylphosphonium bromide; potassium bromide in water; benzene T=70°C; 20 h;