1: 89 percent / Br2, triethylamine / acetic acid / 0.5 h / Heating 2: 1.) methanesulfonic acid, NaNO2, 2.) aq. sodium azide / 1.) H2O, 5 deg C, 24 h, 2.) H2O, 5 deg C 3: 89 percent / KOH / methanol / 1 h / Ambient temperature 4: thionyl chloride / 5 h / Heating 5: 95 percent / pyridine / CH2Cl2 / Ambient temperature 6: 51 percent / BF3*Et2O / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, overnight 7: 5 mg / H2, triethylamine / 10percent Pd/C / 2 h / Ambient temperature 8: 71 percent / NaHCO3 / CHCl3 / 0.33 h View Scheme

1: 69 percent / aq. NaHCO3 / CHCl3 / 0.33 h / Ambient temperature 2: 50 percent / BF3*Et2O / CH2Cl2 / 24 h / Ambient temperature View Scheme