1: 85 percent / iron filings, CaCl2, H2O / ethanol / 16 h / Heating 2: 70 percent / Br2, AcOH / 16 h / Ambient temperature 3: 1.) conc HCl, NaNO2, 2.) 50 percent H3PO2 / 1.) from -10 deg C to 0 deg C, 2 h, 2.) RT, overnight 4: 93 percent / conc. HCl / 16 h / Heating 5: DIBAL-H / toluene / 0.67 h / Heating 7: HOBT, DEC / dimethylformamide / 24 h / 25 °C 8: TFA / CH2Cl2 / 24 h / 25 °C 9: 82 percent / CH2Cl2 / 48 h / 25 °C View Scheme