Multi-step reaction with 9 steps
1.1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2.1: ammonium chloride; iron / ethanol; water / 7 h / 80 °C
3.1: acetic acid / 1,1-dichloroethane / 0.25 h / 20 °C
3.2: 0 - 20 °C
4.1: acetic acid / 1,1-dichloroethane / 0.33 h / 20 °C
4.2: 2 h / 0 - 20 °C
5.1: sodium hydroxide; water / ethanol / 1 h / 60 °C
5.2: pH 7
5.3: pH 5 - 6
6.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / dimethyl sulfoxide / 20 °C
7.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere
8.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 16 h / 20 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 16.17 h / 20 °C / Cooling
With
carbon tetrabromide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; iron; sodium hydride; sodium carbonate; ammonium chloride; acetic acid; triphenylphosphine; sodium hydroxide;
tetrakis(triphenylphosphine) palladium(0);
In
1,4-dioxane; 1,1-dichloroethane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
7.1: Suzuki Coupling;