Multi-step reaction with 11 steps
1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 2.5 h / 20 °C / Cooling with ice
2.1: triethylamine / dichloromethane / 2 h / 20 °C
3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / Cooling with ice
4.1: potassium carbonate / acetonitrile / 20 °C
5.1: sodium hydroxide; water / tetrahydrofuran / 72 h / 20 °C
5.2: 6.5 h / 120 °C
6.1: tetrahydrofuran; methanol / 48 h / 20 °C
7.1: N-Bromosuccinimide; acetic acid / 4 h / 70 °C
8.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 20 °C
9.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C
10.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 110 °C
11.1: hydrogen / 20% palladium(II) hydroxide on carbon / ethanol; tetrahydrofuran / 2 h / 20 °C
With
N-chloro-succinimide; N-Bromosuccinimide; carbon tetrabromide; water; hydrogen; sodium carbonate; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; sodium hydroxide;
tetrakis(triphenylphosphine) palladium(0); 20% palladium(II) hydroxide on carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;