sodium hydrogencarbonate in dichloromethane; water T=15 - 35°C;

lithium aluminium tetrahydride in tetrahydrofuran Heating;

1: 1.) sodamide / 1.) toluene, reflux, 30 min, 2.) toluene, reflux, 30 min 2: 1.) butyl lithium, diisopropylamine / 1.) hexane/THF, 0 to -10 deg C, 10 min, 2.) THF, amb. temp., 1.5 h 3: 88 percent / bromine / CH2Cl2 / 1 h / 30 °C 4: 1.) butyl lithium, diisopropylamine / 1.) hexane/THF, reflux, 3 h, 2.) reflux, 3 h 5: 90 percent / lithium aluminium hydride / tetrahydrofuran / Heating View Scheme

1: 1.) butyl lithium, diisopropylamine / 1.) hexane/THF, 0 to -10 deg C, 10 min, 2.) THF, amb. temp., 1.5 h 2: 88 percent / bromine / CH2Cl2 / 1 h / 30 °C 3: 1.) butyl lithium, diisopropylamine / 1.) hexane/THF, reflux, 3 h, 2.) reflux, 3 h 4: 90 percent / lithium aluminium hydride / tetrahydrofuran / Heating View Scheme

1: 88 percent / bromine / CH2Cl2 / 1 h / 30 °C 2: 1.) butyl lithium, diisopropylamine / 1.) hexane/THF, reflux, 3 h, 2.) reflux, 3 h 3: 90 percent / lithium aluminium hydride / tetrahydrofuran / Heating View Scheme

1: 1.) butyl lithium, diisopropylamine / 1.) hexane/THF, reflux, 3 h, 2.) reflux, 3 h 2: 90 percent / lithium aluminium hydride / tetrahydrofuran / Heating View Scheme