1: 28 percent / KNO3; conc. H2SO4 / 20 h / 80 °C 2: 83 percent / methanol / 0.5 h / 25 - 40 °C 3: 64 percent / PBr3 / CHCl3 / 0.75 h / Heating View Scheme

1.1: 28 percent / KNO3; conc. H2SO4 / 20 h / 80 °C 2.1: 83 percent / methanol / 0.5 h / 25 - 40 °C 3.1: 64 percent / PBr3 / CHCl3 / 0.75 h / Heating 4.1: TMEDA; BuLi / diethyl ether; hexane / 1 h / -70 °C 4.2: 55 percent / diethyl ether; hexane / 1 h / -70 °C 5.1: 75 percent / hydroxylamine hydrochloride; pyridine / ethanol / 0.75 h / Heating View Scheme

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

1.1: 79 percent / m-CPBA / CHCl3 / 13 h / 25 °C 2.1: LDA / hexane; tetrahydrofuran / 0.5 h / -70 °C 2.2: 55 percent / iodine / hexane; tetrahydrofuran / 1 h / -70 °C View Scheme