Multi-step reaction with 14 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / 20 °C / Reflux
1.2: 1.5 h / 20 °C
2.1: sodium hypochlorite / dichloromethane; water / 0.5 h / 20 °C
3.1: n-butyllithium / toluene; hexane; tetrahydrofuran / 0.5 h / -70 °C / Inert atmosphere
3.2: 0.42 h / -70 °C / Inert atmosphere
3.3: 1.25 h / -70 °C / Inert atmosphere
4.1: nitric acid; sulfuric acid / 1 h / Cooling with ice
5.1: ammonium chloride; iron / ethanol; water / 2 h / 20 - 45 °C
6.1: triethylamine / methanol / 4 h / 20 °C
7.1: hydrogen / 5% rhodium-on-charcoal / ethanol / 23 h / 20 °C
8.1: tetrahydrofuran / 14 h / 20 - 70 °C
9.1: potassium carbonate / water; tetrahydrofuran; methanol / 5.5 h / 20 - 50 °C
10.1: triethylamine / water; tetrahydrofuran / 4.5 h / 20 °C / Cooling with ice
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 6 h / 20 °C / Reflux
11.2: 2 h / 20 °C
12.1: acetone / 0.83 h / 20 °C / Cooling with ice
13.1: sulfuric acid / 15.5 h / 20 °C
14.1: triethylamine; p-Chlorothiophenol / ISOPROPYLAMIDE / 2 h / 20 - 60 °C
With
sodium hypochlorite; n-butyllithium; sulfuric acid; hydrogen; nitric acid; iron; potassium carbonate; ammonium chloride; triethylamine; p-Chlorothiophenol; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
5% rhodium-on-charcoal;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; ISOPROPYLAMIDE; water; ethyl acetate; acetone; toluene;