Multi-step reaction with 12 steps
1.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide / dichloromethane; <730 ml / 0.25 h / 0 °C
2.1: 3-chloro-benzenecarboperoxoic acid / 1,1-dichloroethane / 0.33 h / 70 °C
2.2: 0.33 h / 20 °C
3.1: caesium carbonate / N,N-dimethyl-formamide / 1.75 h / 20 °C
4.1: hydrogenchloride; water / ethanol / 0.33 h / 85 °C
5.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
6.1: thionyl chloride; N,N-dimethyl-formamide / tetrahydrofuran / 0.5 h / 0 °C
7.1: N,N-dimethyl-formamide / 2.33 h / 50 °C
8.1: sodium hydride / tetrahydrofuran / 0.25 h / 40 °C
9.1: ethanol / 16 h / 20 - 75 °C
10.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran; ethyl acetate / 2 h / 2068.65 Torr
11.1: acetic acid / 120 °C
12.1: caesium carbonate / N,N-dimethyl-formamide / 1.5 h / 90 °C
With
hydrogenchloride; sodium hypochlorite; thionyl chloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; water; hydrogen; sodium hydride; sodium hydrogencarbonate; caesium carbonate; acetic acid; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; potassium bromide;
palladium 10% on activated carbon;
In
tetrahydrofuran; 1,1-dichloroethane; ethanol; dichloromethane; <730 ml; ethyl acetate; N,N-dimethyl-formamide;