1: lithium methoxide / dimethylformamide / 14 h / 90 °C 2: 92 percent / conc. HCl, H2 / 10 percent Pd/C / acetic acid 3: 98 percent / Br2 / CH2Cl2 4: 68 percent / copper bronze / 2 h / 210 °C 5: 96 percent / LiAlH4 / diethyl ether / 1 h / Heating 6: 88 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / Ambient temperature 7: 96 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature 8: 92 percent / hexamethylphosphoric acid triamide / 2 h / 160 °C View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: 98 percent / K₂CO₃ / acetone / 1.5 h / Heating<br />2: 1.) Br₂, 2.) silver trifluoroacetate in benzene / 1.) CCl₄, a) irrad., reflux, 5.75 h, b) reflux, 1.5 h, 2.) CCl₄, benzene, 2.5 h<br /> <br /> &nbsp;