Multi-step reaction with 13 steps
1.1: Amberlyst.(R). 15 / toluene / 72 h / Heating / reflux
2.1: diphenylether / 0.1 h / 100 - 250 °C
3.1: trichlorophosphate / 2.5 h / Heating / reflux
4.1: hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 0.67 h / 20 °C
4.2: 16 h / Heating / reflux
4.3: 20 °C
5.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C
5.2: 0.5 h / -78 °C
5.3: -78 - 20 °C
6.1: perchloric acid / 2 h / 20 °C
6.2: pH ~ 6
7.1: sodium hydroxide; water / ethanol / 4 h / 20 °C
7.2: pH ~ 3 - ~ 4
8.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 - 35 °C
8.2: 16 h / 20 °C
9.1: lithium hydroxide; water; dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C
9.2: pH ~ 4 - ~ 5
10.1: diethyl ether
11.1: N-Bromosuccinimide / dibenzoyl peroxide / tetrachloromethane / 24 h / 75 °C
12.1: potassium carbonate / N,N-dimethyl-formamide / 1 h
13.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 0.25 h / 110 °C / Microwave irradiation
With
hydrogenchloride; lithium hydroxide; sodium hydroxide; N-Bromosuccinimide; perchloric acid; water; dihydrogen peroxide; potassium hexamethylsilazane; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trichlorophosphate;
tetrakis(triphenylphosphine) palladium(0); dibenzoyl peroxide;
In
tetrahydrofuran; 1,4-dioxane; tetrachloromethane; diphenylether; diethyl ether; ethanol; water; N,N-dimethyl-formamide; toluene;
13.1: Suzuki Coupling;