1.1: aq. H2SO4; sodium 3-nitrobenzene sulfonate / 65 °C 1.2: 70 percent / 4 h / Heating 2.1: 77 percent / aq. HBr / 36 h / Heating View Scheme

1.1: 2 h / 120 °C / Inert atmosphere 2.1: diphenylether / 2 h / Reflux; Inert atmosphere 3.1: sodium hydroxide / water / 3 h / Reflux 4.1: benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere 4.2: 4 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 °C / Inert atmosphere 6.1: palladium diacetate; sodium carbonate; triphenylphosphine / ethylene glycol dimethyl ether; ethanol / 0.17 h / 150 °C / Inert atmosphere; Microwave irradiation View Scheme

1: glycerol With sulfuric acid; m-nitrobenzene sulfonic acid sodium salt T=65°C; 2: 4-Bromo-2-methoxyaniline 4 h; Heating;

(i) NaNO2, aq. HCl, (ii) CuCl; Multistep reaction;

in pyridine; N,N-dimethyl-formamide Reflux;

in tetrahydrofuran 15 h; Heating / reflux;

1: tetrahydrofuran 2: KH; t-BuLi / tetrahydrofuran / -78 °C 3: 80 percent View Scheme

bromine in tetrachloromethane T=20°C; Cooling with ice;

1.1: sulfuric acid; potassium iodide; sodium nitrite / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexanes / -80 °C / Inert atmosphere 2.2: -80 - 20 °C / Inert atmosphere 2.3: 20 °C / Inert atmosphere View Scheme

calcium sulfate; acetic acid in ethanol 4 h; Heating;