Multi-step reaction with 10 steps
1.1: acetic acid / dichloromethane / 1.08 h / 10 °C
1.2: 18 h / 10 - 20 °C
2.1: hydrogen / 3percent Pt/0.6percentVG/C, deGussa / ethanol / 2.5 h / 10 °C / 2068.65 Torr / Inert atmosphere
3.1: methanesulfonic acid; isopentyl nitrite / ethanol / 0.25 h
4.1: boron tribromide / dichloromethane / 3 h / 0 - 20 °C
4.2: 15 h
4.3: pH < 5
5.1: N-iodo-succinimide / acetic acid / 0.25 h
6.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 50 °C
7.1: copper(l) iodide / N,N-dimethyl-formamide / 1.5 h / 100 °C
8.1: hydrogen / 10 wt% Pd(OH)2 on carbon / ethyl acetate; methanol / 1.5 h / 760.05 Torr / Inert atmosphere
9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h / 0 °C
10.1: potassium phosphate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1 h / 90 °C
With
potassium phosphate; N-iodo-succinimide; copper(l) iodide; methanesulfonic acid; hydrogen; boron tribromide; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; isopentyl nitrite;
tetrakis(triphenylphosphine) palladium(0); 10 wt% Pd(OH)2 on carbon;
In
1,4-dioxane; methanol; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide;