Multi-step reaction with 8 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 16 - 25 °C
1.2: 24 h / 110 °C
2.1: hydrogen; sodium acetate / 10 % Pd(OH)2/C / ethanol / 18 h / 1810.07 Torr
3.1: bromine / chloroform / 1 h / 0 °C
4.1: tetrahydrofuran / 20 °C
5.1: sodium hydroxide / tetrahydrofuran; water / Heating / reflux
6.1: N-ethyl-N,N-diisopropylamine / ethanol / 20 - 60 °C
7.1: N-ethyl-N,N-diisopropylamine / tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 2 h / 95 °C
8.1: potassium tert-butylate / dimethyl sulfoxide / 2 h / 20 °C
With
sodium hydroxide; potassium tert-butylate; hydrogen; bromine; sodium acetate; sodium hydride; N-ethyl-N,N-diisopropylamine;
tris-(dibenzylideneacetone)dipalladium(0); 10 % Pd(OH)2/C; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
tetrahydrofuran; 1,4-dioxane; ethanol; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide;