manganese(IV) oxide in dichloromethane T=25°C; 36 h;

1: 76 percent / N-bromosuccinimide / tetrahydrofuran / 3 h / Ambient temperature 2: 1.) butyllithium / 1.) hexane, THF, -78 deg C, 15 min, 2.) hexane, THF, 30 min 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 30 min, 2.) CH2Cl2, from -60 deg C to RT View Scheme

1: 100 percent / hydrogen / platinum(IV) oxide / ethanol / 2.5 h / 760 Torr 2: 94 percent / pyridine / 72 h / Ambient temperature 3: 76 percent / 6 M aq. HCl / dioxane / 24 h / Heating 4: 76 percent / N-bromosuccinimide / tetrahydrofuran / 3 h / Ambient temperature 5: 1.) butyllithium / 1.) hexane, THF, -78 deg C, 15 min, 2.) hexane, THF, 30 min 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 30 min, 2.) CH2Cl2, from -60 deg C to RT View Scheme

1: 100 percent / benzene / 5.25 h / Heating 2: 100 percent / hydrogen / platinum(IV) oxide / ethanol / 2.5 h / 760 Torr 3: 94 percent / pyridine / 72 h / Ambient temperature 4: 76 percent / 6 M aq. HCl / dioxane / 24 h / Heating 5: 76 percent / N-bromosuccinimide / tetrahydrofuran / 3 h / Ambient temperature 6: 1.) butyllithium / 1.) hexane, THF, -78 deg C, 15 min, 2.) hexane, THF, 30 min 7: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 30 min, 2.) CH2Cl2, from -60 deg C to RT View Scheme

1: 1.) butyllithium / 1.) hexane, THF, -78 deg C, 15 min, 2.) hexane, THF, 30 min 2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 30 min, 2.) CH2Cl2, from -60 deg C to RT View Scheme

1: 94 percent / pyridine / 72 h / Ambient temperature 2: 76 percent / 6 M aq. HCl / dioxane / 24 h / Heating 3: 76 percent / N-bromosuccinimide / tetrahydrofuran / 3 h / Ambient temperature 4: 1.) butyllithium / 1.) hexane, THF, -78 deg C, 15 min, 2.) hexane, THF, 30 min 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 30 min, 2.) CH2Cl2, from -60 deg C to RT View Scheme

1: 76 percent / 6 M aq. HCl / dioxane / 24 h / Heating 2: 76 percent / N-bromosuccinimide / tetrahydrofuran / 3 h / Ambient temperature 3: 1.) butyllithium / 1.) hexane, THF, -78 deg C, 15 min, 2.) hexane, THF, 30 min 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 30 min, 2.) CH2Cl2, from -60 deg C to RT View Scheme