1: 92 percent / conc. HCl, H2 / 10 percent Pd/C / acetic acid 2: 98 percent / Br2 / CH2Cl2 3: 68 percent / copper bronze / 2 h / 210 °C 4: 96 percent / LiAlH4 / diethyl ether / 1 h / Heating 5: 88 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / Ambient temperature 6: 96 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature 7: 92 percent / hexamethylphosphoric acid triamide / 2 h / 160 °C View Scheme