hydrogenchloride 48 h; 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: 90 percent / aq. sodium hydroxide / Ambient temperature 5: 1.) sodium amide / 1.) toluene, reflux, 2 h, 2.) THF, 2 h 6: 84 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / Heating 7: 92 percent / 12 M hydrochloric acid / 48 h / 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: 90 percent / aq. sodium hydroxide / Ambient temperature 4: 1.) sodium amide / 1.) toluene, reflux, 2 h, 2.) THF, 2 h 5: 84 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / Heating 6: 92 percent / 12 M hydrochloric acid / 48 h / Heating View Scheme

1: 1.) butyl lithium, 2,2,6,6-tetramethylpiperidine / 1.) hexane/THF, 0 deg C, 10 min, 2.) 30 min 2: 1.) sodium amide / 1.) toluene, reflux, 2 h, 2.) THF, 2 h 3: 84 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / Heating 4: 92 percent / 12 M hydrochloric acid / 48 h / Heating View Scheme

1: 88 percent / bromine / CH2Cl2 / 1 h / 30 °C 2: 90 percent / aq. sodium hydroxide / Ambient temperature 3: 1.) sodium amide / 1.) toluene, reflux, 2 h, 2.) THF, 2 h 4: 84 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / Heating 5: 92 percent / 12 M hydrochloric acid / 48 h / Heating View Scheme

1: 90 percent / aq. sodium hydroxide / Ambient temperature 2: 1.) sodium amide / 1.) toluene, reflux, 2 h, 2.) THF, 2 h 3: 84 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / Heating 4: 92 percent / 12 M hydrochloric acid / 48 h / Heating View Scheme

1: 1.) sodium amide / 1.) toluene, reflux, 2 h, 2.) THF, 2 h 2: 84 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / Heating 3: 92 percent / 12 M hydrochloric acid / 48 h / Heating View Scheme

1: 84 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / Heating 2: 92 percent / 12 M hydrochloric acid / 48 h / Heating View Scheme

hydrogenchloride; hydrogen; palladium on activated charcoal 1.) ethanol/water, 50 psi, 10 min, 2.) propan-2-ol/ether; Yield given. Multistep reaction;

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