1: 1.) KOH, 2.) KMnO4, MgSO4 / 1.) MeOH, 0 deg C, 15 min, 2.) MeOH, H2O, 0 deg C, 2 h 2: 80 percent / NaBH4 / ethanol / 0.5 h / Ambient temperature 3: Et3N / CH2Cl2 / 1 h / Ambient temperature 4: NaI / tetrahydrofuran / 48 h / Heating 5: 82 percent / NaOH, H2O / ethanol / 0.5 h / 78 °C 6: 1.) HCl, 2.) Br2 / 1.) EtOH, 78 deg C, 30 min, 2.) CHCl3, 61 deg C, 30 min View Scheme

hydrogenchloride; bromine 1.) EtOH, 78 deg C, 30 min, 2.) CHCl3, 61 deg C, 30 min; Yield givenMultistep reaction;