Multi-step reaction with 13 steps
1.1: bromine; acetic acid / methanol / 2 h / 20 °C / Cooling with ice
2.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C
2.2: 4 h / 0 - 50 °C
3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / -78 - 20 °C
3.2: 1 h / 20 °C
4.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 20 °C
4.2: pH 1
5.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C
6.1: triethylamine / dmap / 1 h / 20 °C
7.1: boron tribromide / dichloromethane / 0.58 h / -78 - 0 °C
7.2: 0.33 h / 20 °C
8.1: [bis(acetoxy)iodo]benzene / 1,4-dioxane / 17 h / 0 - 20 °C
8.2: 0.33 h / 20 °C
9.1: potassium carbonate / acetone / 2 h / Reflux
10.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene / 90 °C / Inert atmosphere
11.1: hydrogen / 30 wt % Pd/C / methanol / 1 h / 20 °C
12.1: dmap / dichloromethane / 1.5 h / 20 °C
13.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine / tetrahydrofuran / 0.5 h / -78 °C
13.2: 1 h / -100 - -20 °C
With
hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; [bis(acetoxy)iodo]benzene; hydrogen; bromine; boron tribromide; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; diisopropylamine; sodium nitrite;
dmap; tetrakis(triphenylphosphine) palladium(0); 30 wt % Pd/C; N,N-dimethyl-formamide;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol;