aluminium trichloride in chloroform T=20°C; 5 h;

1: 91 percent / Zn / H2O; acetic acid / 2.5 h / Heating 2: 1) NaOH, Cl2 / 1) H2O, -10 deg C, 2) 50 deg C View Scheme

sodium hypochlorite

1: 91 percent / Zn / H2O; acetic acid / 2.5 h / Heating 2: 93 percent / Cl2, AlCl3 / CHCl3; CCl4 / 1.5 h / 30 °C 3: 1) NaOH, Cl2 / 1) H2O, -10 deg C, 2) 50 deg C View Scheme

sodium tetrahydroborate; hydrogen; CaO; palladium in ethanol T=20°C; P=760 Torr; other temperature, other solvent, other acceptor; Rate constant;

1.1: thiourea / ethanol; water / 2 h / |Reflux; |Large scale 1.2: 3 h / |Reflux; |Large scale 2.1: chlorine / toluene / 0.42 h / 8 °C / |Cooling with ice 3.1: ammonia / 1 h / 5 - 15 °C 4.1: Na2WO4·2H2O; dihydrogen peroxide / water / 19 h / 15 - 35 °C 5.1: pyridinium tribromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / |Large scale 6.1: bis[(1S,2R,3S,5S)-pinan-3-yl]chloroborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / |Inert atmosphere 6.2: 2 h / 0 - 22 °C 7.1: potassium carbonate / dimethyl sulfoxide 8.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -70 - -66 °C / |Inert atmosphere 8.2: 20 °C / pH 4 8.3: 15 h / 0 - 25 °C 9.1: acetonitrile / 19 h / 30 - 85 °C / |Reflux 10.1: triethylamine / tetrahydrofuran / 2 h / -10 - -2 °C / |Inert atmosphere 11.1: water / 15 h / 11 - 20 °C View Scheme

1.1: thiourea / ethanol; water / 2 h / |Reflux; |Large scale 1.2: 3 h / |Reflux; |Large scale 2.1: chlorine / toluene / 0.42 h / 8 °C / |Cooling with ice 3.1: ammonia / 1 h / 5 - 15 °C 4.1: Na2WO4·2H2O; dihydrogen peroxide / water / 19 h / 15 - 35 °C 5.1: pyridinium tribromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / |Large scale 6.1: bis[(1S,2R,3S,5S)-pinan-3-yl]chloroborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / |Inert atmosphere 6.2: 2 h / 0 - 22 °C 7.1: potassium carbonate / dimethyl sulfoxide 8.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -70 - -66 °C / |Inert atmosphere 8.2: 20 °C / pH 4 8.3: 15 h / 0 - 25 °C View Scheme

sodium hydroxide; thiourea in tetrahydrofuran; water

1: benzyl chloride With thiourea in ethanol; water 2 h; RefluxLarge scale; 2: 3-acetyl-2,5-dichlorothiophene With sodium hydroxide in ethanol; water 3 h; RefluxLarge scale; regioselective reaction;

1.1: thiourea / ethanol; water / 2 h / |Reflux; |Large scale 1.2: 3 h / |Reflux; |Large scale 2.1: chlorine / toluene / 0.42 h / 8 °C / |Cooling with ice 3.1: ammonia / 1 h / 5 - 15 °C 4.1: Na2WO4·2H2O; dihydrogen peroxide / water / 19 h / 15 - 35 °C 5.1: pyridinium tribromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / |Large scale 6.1: bis[(1S,2R,3S,5S)-pinan-3-yl]chloroborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / |Inert atmosphere 6.2: 2 h / 0 - 22 °C 7.1: potassium carbonate / dimethyl sulfoxide View Scheme