1: With sulfuric acid; sodium nitrite in water T=0°C; 1 h; 2: With sodium iodide in water T=0 - 20°C; 12 h;

hydrogen iodide; iodine; acetic anhydride; acetic acid; H-β-form zeolite T=122°C; 4 h; Product distribution / selectivity;

sulfuric acid; iodine cloride; periodic acid; H-β zeolite in water; acetic acid T=90°C; 5.66667 h; Product distribution / selectivity;

1: H2 / Pd/C / dimethylformamide / 2223.7 Torr 2: 1.) NaNO2, HCl; 2.) KI / 1.) DMF View Scheme

sodium hydroxide

1: (i) NaNO2, aq. H2SO4, (ii) KI 2: aq. NaOH View Scheme

1: 54 percent / trimethyl borate, BH3*Me2S / tetrahydrofuran / 1.5 h / Ambient temperature 2: 86 percent / LiBr, p-TsOH / Ambient temperature 3: 1.) Mg, 1,2-dibromoethane / 1.) THF, reflux, 6.5 h, 2.) THF, RT, overnight 4: 90 percent / MnO2 / CHCl3 / 1 h / Heating 5: 51 percent / KOH, hydrazine hydrate / ethane-1,2-diol / 2 h / 200 °C 6: 58 percent / aq. HCl / 2.5 h / 110 - 120 °C View Scheme

thionyl chloride T=0°C; 3 h; Heating / reflux;