Multi-step reaction with 11 steps
1.1: nitric acid; sulfuric acid / 2.58 h / -10 - 100 °C
1.2: 40 °C / pH 8
2.1: N-Bromosuccinimide; acetic acid / 2 h / 60 °C
2.2: 0.5 h / 80 °C
3.1: hydrogen / Raney nickel / ethanol / 12 h / 20 °C
4.1: acetic anhydride / 4 h / 120 °C / Inert atmosphere
5.1: N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 0.17 h / -60 °C / Inert atmosphere
5.2: 2 h
6.1: thionyl chloride / 2 h / 75 °C
6.2: 10 h / 0 - 20 °C
7.1: trichlorophosphate / 3 h / 90 °C
8.1: triethylamine / tetrahydrofuran / 12 h / 0 - 20 °C
9.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 14 h / 65 °C / Inert atmosphere
10.1: caesium carbonate / tricyclohexylphosphine; palladium diacetate / toluene / 12 h / 95 °C / Inert atmosphere
11.1: water; sulfuric acid / 0.5 h / 0 - 95 °C
11.2: pH 8 - 9
With
N-Bromosuccinimide; thionyl chloride; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; water; hydrogen; nitric acid; acetic anhydride; caesium carbonate; acetic acid; triethylamine; trichlorophosphate;
tetrakis(triphenylphosphine) palladium(0); palladium diacetate; tricyclohexylphosphine;
In
tetrahydrofuran; ethanol; toluene;