Multi-step reaction with 13 steps
1.1: toluene / 1 h / 100 °C
2.1: bromine / acetic acid / 3 h / 20 °C
3.1: acetic anhydride; potassium acetate; isopentyl nitrate / 18-crown-6 ether / chloroform / 3 h / 65 °C
4.1: hydrogenchloride / water; methanol / 1 h / 100 °C
4.2: Cooling with ice
5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 20 °C
5.2: 1.5 h / Cooling with ice
6.1: triethylamine / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 9 h / 90 °C
7.1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide; α,α,α-trifluorotoluene / α,α,α-trifluorotoluene / 0.55 h / 20 - 130 °C
8.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C
9.1: potassium hydroxide; water / ethanol / 5 h / 40 °C
10.1: polyphosphoric acid / 1 h / 90 °C
11.1: n-propyltriphenylphosphonium bromide / tetrahydrofuran / 2 h / -10 - 20 °C
11.2: 12 h / 20 °C
12.1: 4-(dimethylamino)-pyridinium tribromide / acetonitrile / 4 h / 80 °C
13.1: sodium carbonate / triphenylphosphine; palladium diacetate / 1,4-dioxane; water / 7 h / 70 °C
With
hydrogenchloride; N-Bromosuccinimide; isopentyl nitrate; 2,2'-azobis(isobutyronitrile); α,α,α-trifluorotoluene; 4-(dimethylamino)-pyridinium tribromide; water; bromine; potassium acetate; n-propyltriphenylphosphonium bromide; acetic anhydride; sodium hydride; sodium carbonate; potassium carbonate; triethylamine; potassium hydroxide;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 18-crown-6 ether; palladium diacetate; triphenylphosphine;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; chloroform; α,α,α-trifluorotoluene; water; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;