lithium aluminium tetrahydride in diethyl ether 96 h; Ambient temperature;

in benzene T=50°C; 2 h;

1: 95 percent / hydrochloric acid / aq. ethanol 2: 68 percent / sodium hydride / CH2Cl2 3: 53 percent / chlorobenzene / 0.5 h / Heating 4: 97 percent / lithium aluminum hydride / diethyl ether / 96 h / Ambient temperature View Scheme

1: N-chlorosuccinimide, dimethyl sulfide, triethylamine / toluene / -20 °C 2: 95 percent / hydrochloric acid / aq. ethanol 3: 68 percent / sodium hydride / CH2Cl2 4: 53 percent / chlorobenzene / 0.5 h / Heating 5: 97 percent / lithium aluminum hydride / diethyl ether / 96 h / Ambient temperature View Scheme

1: 68 percent / sodium hydride / CH2Cl2 2: 53 percent / chlorobenzene / 0.5 h / Heating 3: 97 percent / lithium aluminum hydride / diethyl ether / 96 h / Ambient temperature View Scheme

2: 86 percent / thionyl chloride / methanol / 6 h / Heating 3: 88 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 4: 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / 1.) tolueene, - 25 deg C, 2.5 h, 2.) -25 deg C -> 25 deg C; other reagents 5: 94 percent / hydrochloric acid / aq. ethanol 6: 1.) sodium hydride / 1.) dichloromethane, 2.) chlorobenzene, 120 deg C, 0.5 h 7: lithium aluminum hydride / diethyl ether / Ambient temperature View Scheme

1: 88 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 2: 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / 1.) tolueene, - 25 deg C, 2.5 h, 2.) -25 deg C -> 25 deg C; other reagents 3: 94 percent / hydrochloric acid / aq. ethanol 4: 1.) sodium hydride / 1.) dichloromethane, 2.) chlorobenzene, 120 deg C, 0.5 h 5: lithium aluminum hydride / diethyl ether / Ambient temperature View Scheme

1: 86 percent / thionyl chloride / methanol / 6 h / Heating 2: 88 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 3: 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / 1.) tolueene, - 25 deg C, 2.5 h, 2.) -25 deg C -> 25 deg C; other reagents 4: 94 percent / hydrochloric acid / aq. ethanol 5: 1.) sodium hydride / 1.) dichloromethane, 2.) chlorobenzene, 120 deg C, 0.5 h 6: lithium aluminum hydride / diethyl ether / Ambient temperature View Scheme

1: 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / 1.) tolueene, - 25 deg C, 2.5 h, 2.) -25 deg C -> 25 deg C; other reagents 2: 94 percent / hydrochloric acid / aq. ethanol 3: 1.) sodium hydride / 1.) dichloromethane, 2.) chlorobenzene, 120 deg C, 0.5 h 4: lithium aluminum hydride / diethyl ether / Ambient temperature View Scheme

1: 94 percent / hydrochloric acid / aq. ethanol 2: 1.) sodium hydride / 1.) dichloromethane, 2.) chlorobenzene, 120 deg C, 0.5 h 3: lithium aluminum hydride / diethyl ether / Ambient temperature View Scheme