1: NaOMe / benzene / 8 h / Heating 2: 70 percent / aq. KOH / methanol / Heating 3: 1.) HgO, MgSO4, 2.) Br2 / 1.) CH2Cl2, reflux, 15 min, 2.) CH2Cl2, reflux, 3.5 h 4: 1.) THF, pentane, -78 deg C, 5 min, 2.) THF, pentane, from -78 deg C to RT View Scheme

1: 70 percent / aq. KOH / methanol / Heating 2: 1.) HgO, MgSO4, 2.) Br2 / 1.) CH2Cl2, reflux, 15 min, 2.) CH2Cl2, reflux, 3.5 h 3: 1.) THF, pentane, -78 deg C, 5 min, 2.) THF, pentane, from -78 deg C to RT View Scheme

1: 1.) HgO, MgSO4, 2.) Br2 / 1.) CH2Cl2, reflux, 15 min, 2.) CH2Cl2, reflux, 3.5 h 2: 1.) THF, pentane, -78 deg C, 5 min, 2.) THF, pentane, from -78 deg C to RT View Scheme

1.) THF, pentane, -78 deg C, 5 min, 2.) THF, pentane, from -78 deg C to RT; Yield given. Multistep reaction;