1: Br2 / I2 / CH2Cl2 / Ambient temperature 2: NEt3 / tetrahydrofuran / Ambient temperature 3: NaBH4 / methanol / 0 degC to room temp. 4: aq. H2SO4; tetrahydrofuran / Heating 5: NaOAc 7: aq. HCl / Heating 8: 99 percent / aq. 2M Na2CO3 / Pd(PPh3)4 / benzene / Heating 9: 85 percent / 1) NaNO2, dil. HCl, 2) NaN3 / 1) 0 degC 10: 96 percent / various solvent(s) / 180 °C View Scheme