Multi-step reaction with 12 steps
1.1: potassium nitrite; sulfuric acid / 2 h / 20 °C
2.1: thionyl chloride / Reflux
3.1: hydrogen; palladium 10% on activated carbon / 760.05 Torr
4.1: sodium nitrite; hydrogen bromide / water / 0.5 h / 0 °C
4.2: 1 h / 0 - 20 °C
5.1: methyl magnesium iodide / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere
6.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1.5 h / 100 °C / Microwave irradiation
7.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 80 °C / Inert atmosphere
8.1: hydrogenchloride / tetrahydrofuran; water / 20 °C
9.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 16 h / Reflux
10.1: hydroxylamine hydrochloride; sodium acetate / tetrahydrofuran; water / 2 h / 20 °C
11.1: N-chloro-succinimide / N,N-dimethyl-formamide / 3 h / 45 °C
12.1: triethylamine / N,N-dimethyl-formamide / 12 h / 20 °C
With
hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-chloro-succinimide; N-Bromosuccinimide; methyl magnesium iodide; thionyl chloride; potassium nitrite; sulfuric acid; palladium 10% on activated carbon; hydroxylamine hydrochloride; hydrogen bromide; hydrogen; potassium acetate; sodium acetate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium nitrite; dibenzoyl peroxide;
In
tetrahydrofuran; 1,4-dioxane; tetrachloromethane; water; N,N-dimethyl-formamide;