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: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); zinc diacetate; zinc / water; N,N-dimethyl-formamide / 18 h / 100 °C / Inert atmosphere; Sealed tube
10.1: formic acid / aluminum nickel alloy / water / 5 h / 95 °C / Inert atmosphere
10.2: pH 9
11.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 105 °C / Inert atmosphere; Sealed tube
With
formic acid; tin(II) chloride dihdyrate; sulfuric acid; water; bromine; potassium carbonate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; sodium nitrite;
1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); zinc diacetate; zinc;
In
tetrahydrofuran; 1,4-dioxane; ethanol; water; N,N-dimethyl-formamide; acetone; acetonitrile;