Multi-step reaction with 11 steps
1.1: bromine / acetonitrile / 1 h / 30 - 35 °C / Industry scale
2.1: sulfuric acid; sodium nitrite / ethanol / -10 - 55 °C
3.1: potassium carbonate / acetone / 3 h / Reflux; Industry scale
4.1: tin(II) chloride dihdyrate / tetrahydrofuran / 3 h / Reflux; Industry scale
4.2: 0 - 5 °C
5.1: acetone / 0.75 h / 20 °C
6.1: water; sodium hydroxide / tetrahydrofuran / 69 - 70 °C
7.1: bromine / acetonitrile / 1.5 h / 0 - 20 °C
8.1: 1,4-dioxane / 80 - 85 °C
9.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere
10.1: hydrogenchloride; water / tetrahydrofuran / 4 h / 20 °C
11.1: N,N-dimethyl-formamide / 2 h / 60 °C
With
hydrogenchloride; tin(II) chloride dihdyrate; sulfuric acid; water; bromine; potassium carbonate; sodium hydroxide; sodium nitrite;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; ethanol; N,N-dimethyl-formamide; acetone; acetonitrile;