sodium carbonate in dichloromethane; water T=0 - 20°C;

1: sodium carbonate / water; dichloromethane; toluene / 1 h / 20 - 35 °C / |Inert atmosphere; |Large scale 2: sodium tetrahydroborate / methanol; tetrahydrofuran / 2.5 h / 50 °C / |Inert atmosphere; |Reflux; |Large scale 3: sodium bromide; sodium hydrogencarbonate; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; sodium hypochlorite / water; dichloromethane / 0.33 h / 10 °C / |Inert atmosphere; |Large scale 4: sodium tris(acetoxy)borohydride / ethyl acetate / 2 h / 0 - 15 °C / |Inert atmosphere; |Large scale View Scheme

thionyl chloride in toluene T=92°C; 2.5 h; Inert atmosphereLarge scale;

in toluene 2 h; Heating / reflux;

1.1: diethylamino-sulfur trifluoride / dichloromethane / 0 - 20 °C / |Inert atmosphere 1.2: 20 h / |Inert atmosphere 2.1: sodium hydroxide / water; methanol / 15 h / 20 °C / |Inert atmosphere 3.1: thionyl chloride / toluene / 2.5 h / 92 °C / |Inert atmosphere; |Large scale View Scheme

1: sodium hydroxide / water; methanol / 15 h / 20 °C / |Inert atmosphere 2: thionyl chloride / toluene / 2.5 h / 92 °C / |Inert atmosphere; |Large scale View Scheme

ammonia in water; toluene T=40°C; 1.61667 h;

1: sodium carbonate / water; dichloromethane; toluene / 1 h / 20 - 35 °C / |Inert atmosphere; |Large scale 2: sodium tetrahydroborate / methanol; tetrahydrofuran / 2.5 h / 50 °C / |Inert atmosphere; |Reflux; |Large scale View Scheme