1: in acetonitrile T=20°C; 5 h; Heating / reflux; 2: With potassium hydroxide in water; ethyl acetate; acetonitrile

1: (+/-)-1-(3-chlorophenyl)-2-hydroxypropan-1-one With 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride in dichloromethane T=-40°C; 0.5 h; 2: tert-butylamine in dichloromethane 12 h; Further stages.;

bromine 1.) MeOH, 2.) CH3CN; Multistep reaction;

1: bromine / CH2Cl2 / cooling 2: 1-methyl-pyrrolidin-2-one / 0.17 h / 50 - 60 °C View Scheme

1: ethanol 2: 1.) Br2 / 1.) MeOH, 2.) CH3CN View Scheme

1: 1.) SOCl2, 2.) NH4OH, 3.) SOCl2 / 2.) dioxane, 3.) reflux 2: ethanol 3: 1.) Br2 / 1.) MeOH, 2.) CH3CN View Scheme

1.1: water; lithium hydroxide hydrate / acetonitrile / 4 h / 50 - 60 °C 2.1: triethylamine / acetone / 0.08 h / 0 °C 3.1: sodium azide / acetone / 2 h / 20 °C 4.1: toluene / 2 h / Reflux; Inert atmosphere 5.1: water / 2 h / Reflux 6.1: sodium tetrahydroborate / methanol / 0.17 h / 0 - 20 °C / Inert atmosphere 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 30 h / 20 °C 9.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.5 h / -78 - -40 °C 9.2: 14 h / -40 - 0 °C View Scheme

1.1: triethylamine / acetone / 0.08 h / 0 °C 2.1: sodium azide / acetone / 2 h / 20 °C 3.1: toluene / 2 h / Reflux; Inert atmosphere 4.1: water / 2 h / Reflux 5.1: sodium tetrahydroborate / methanol / 0.17 h / 0 - 20 °C / Inert atmosphere 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 30 h / 20 °C 8.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.5 h / -78 - -40 °C 8.2: 14 h / -40 - 0 °C View Scheme

1.1: sodium tetrahydroborate / methanol / 0.17 h / 0 - 20 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 30 h / 20 °C 4.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.5 h / -78 - -40 °C 4.2: 14 h / -40 - 0 °C View Scheme

1.1: 1,4-diaza-bicyclo[2.2.2]octane / 30 °C / Sonication 2.1: 1H-imidazole; dimethyl sulfoxide / 20 °C / Inert atmosphere 3.1: water; lithium hydroxide hydrate / acetonitrile / 4 h / 50 - 60 °C 4.1: triethylamine / acetone / 0.08 h / 0 °C 5.1: sodium azide / acetone / 2 h / 20 °C 6.1: toluene / 2 h / Reflux; Inert atmosphere 7.1: water / 2 h / Reflux 8.1: sodium tetrahydroborate / methanol / 0.17 h / 0 - 20 °C / Inert atmosphere 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C 10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 30 h / 20 °C 11.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.5 h / -78 - -40 °C 11.2: 14 h / -40 - 0 °C View Scheme