1: With lithium diisopropyl amide in tetrahydrofuran; hexane T=-70°C; Metallation; 0.5 h; 2: With bromocyane in tetrahydrofuran; hexane T=-70°C; Bromination; 0.25 h;

tetrakis(triphenylphosphine) palladium(0) in toluene 16 h; Heating;

1.1: 79 percent / m-CPBA / CHCl3 / 13 h / 25 °C 2.1: LDA / hexane; tetrahydrofuran / 0.5 h / -70 °C 2.2: 70 percent / BrCN / hexane; tetrahydrofuran / 0.25 h / -70 °C View Scheme

sulfuric acid; potassium nitrate T=80°C; Nitration; 20 h;

1: 66 percent / KNO3; conc. H2SO4 / 20 h / 80 °C 2: 84 percent / methanol / 0.5 h / 25 - 40 °C 3: 90 percent / PBr3 / CHCl3 / 0.75 h / Heating View Scheme

1: 66 percent / KNO3; conc. H2SO4 / 20 h / 80 °C 2: 84 percent / methanol / 0.5 h / 25 - 40 °C 3: 90 percent / PBr3 / CHCl3 / 0.75 h / Heating 4: 90 percent / Pd(PPh3)4 / tetrahydrofuran / 40 h / Heating 5: 64 percent / benzeneselenic anhydride / dioxane / 24 h / Heating 6: 75 percent / hydroxylamine hydrochloride; pyridine / ethanol / 0.75 h / Heating View Scheme

1: 66 percent / KNO3; conc. H2SO4 / 20 h / 80 °C 2: 84 percent / methanol / 0.5 h / 25 - 40 °C 3: 90 percent / PBr3 / CHCl3 / 0.75 h / Heating 4: 90 percent / Pd(PPh3)4 / tetrahydrofuran / 40 h / Heating View Scheme