1: diisopropylethylamine / CH2Cl2 / 0.67 h / -20 °C 2: Br2 / CH2Cl2 / -20 --> 0 deg C, then 0 deg C, 10 min 3: propan-2-ol; acetonitrile; CHCl3; H2O View Scheme

1: 88 percent / KH (22percent) / benzene / 2 h / Heating 2: 87 percent / H2 / palladium black / methanol; acetic acid / 760 Torr / Ambient temperature 3: 1.) KH / 1.) benzene, room temp.; 2.) room temp., 2 h 4: 98 percent / HCl (6N) / tetrahydrofuran / 0.08 h / Ambient temperature 5: 1.) Pb(OAc)4; 2.) NaBH4 / 1.) benzene, room temp.; 2.) MeOH, THF, room temp. 6: 2.) AgOAc / 1.) methanol, 55 deg C, overnight; 2.) 90 percent aqueous methanol, 2 h View Scheme

1: 80 percent / BF3 etherate / CHCl3 / 24 h 2: 90 percent / 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 16 h / Heating 3: 81 percent / potassium superoxide / 18-crown-6 / dimethylsulfoxide; dimethylformamide; 1,2-dimethoxy-ethane / 6 h / Ambient temperature 4: 100 percent / triethylamine / benzene / 2 h / Ambient temperature 5: acetonitrile / 36 h / 65 - 70 °C View Scheme

1: 81 percent / potassium superoxide / 18-crown-6 / dimethylsulfoxide; dimethylformamide; 1,2-dimethoxy-ethane / 6 h / Ambient temperature 2: 100 percent / triethylamine / benzene / 2 h / Ambient temperature 3: acetonitrile / 36 h / 65 - 70 °C View Scheme

1: 90 percent / 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 16 h / Heating 2: 81 percent / potassium superoxide / 18-crown-6 / dimethylsulfoxide; dimethylformamide; 1,2-dimethoxy-ethane / 6 h / Ambient temperature 3: 100 percent / triethylamine / benzene / 2 h / Ambient temperature 4: acetonitrile / 36 h / 65 - 70 °C View Scheme

in acetonitrile T=65°C; 24 h; in a pressure bottle; Yield given;

1: 87 percent / H2 / palladium black / methanol; acetic acid / 760 Torr / Ambient temperature 2: 1.) KH / 1.) benzene, room temp.; 2.) room temp., 2 h 3: 98 percent / HCl (6N) / tetrahydrofuran / 0.08 h / Ambient temperature 4: 1.) Pb(OAc)4; 2.) NaBH4 / 1.) benzene, room temp.; 2.) MeOH, THF, room temp. 5: 2.) AgOAc / 1.) methanol, 55 deg C, overnight; 2.) 90 percent aqueous methanol, 2 h View Scheme

1: 90 percent / HCl gas / CHCl3; methanol / 0.75 h / Ambient temperature 2: triethylamine / benzene / 2 h / Ambient temperature 3: acetonitrile / 24 h / 65 °C View Scheme

1: 98 percent / sodium hydride / benzene / 12 h / Ambient temperature 2: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 3: 100 percent / triethylamine / benzene / 2 h / Ambient temperature 4: acetonitrile / 36 h / 65 - 70 °C View Scheme

1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 2: 100 percent / triethylamine / benzene / 2 h / Ambient temperature 3: acetonitrile / 36 h / 65 - 70 °C View Scheme