1: 48percent aq. HBr / H2O / 24 h / 80 °C 2: 95 percent / Amberlyst H-15 / hexane / 8 h / Ambient temperature 4: 94 percent / FeCl3 / diethyl ether / Ambient temperature 5: 1.) 1.6 M n-BuLi, 2.) ZnBr2, tetrakis triphenyl phosphine palladium (3percent) / 1.) Et2O, -60 deg C, 30 min, 2.) THF, RT 6: 2N KOH / methanol 7: PDC / CH2Cl2 / 6 h / Ambient temperature View Scheme

1: 95 percent / Amberlyst H-15 / hexane / 8 h / Ambient temperature 3: 94 percent / FeCl3 / diethyl ether / Ambient temperature 4: 1.) 1.6 M n-BuLi, 2.) ZnBr2, tetrakis triphenyl phosphine palladium (3percent) / 1.) Et2O, -60 deg C, 30 min, 2.) THF, RT 5: 2N KOH / methanol 6: PDC / CH2Cl2 / 6 h / Ambient temperature View Scheme