1: 1.) n-BuLi / 1.) THF, -20 deg C 2: 1.) n-BuLi / 1.) THF, -20 deg C 3: 91 percent / Et3N, 4-dimethylaminopyridine (DMAP) / CH2Cl2 4: 84 percent / TsOH / methanol 5: DMSO, py, TFA, DCC / benzene 6: AgNO3, aq. NaOH / tetrahydrofuran 7: 53 percent / aq. NaOH / methanol 8: 47 percent / 2,4,6-Cl3C6H2COCl, Et3N, DMAP / toluene / Heating 9: 42 percent / N-bromosuccinimide (NBS), H2O / acetone View Scheme

1: 1.) n-BuLi / 1.) THF, -20 deg C 2: 91 percent / Et3N, 4-dimethylaminopyridine (DMAP) / CH2Cl2 3: 84 percent / TsOH / methanol 4: DMSO, py, TFA, DCC / benzene 5: AgNO3, aq. NaOH / tetrahydrofuran 6: 53 percent / aq. NaOH / methanol 7: 47 percent / 2,4,6-Cl3C6H2COCl, Et3N, DMAP / toluene / Heating 8: 42 percent / N-bromosuccinimide (NBS), H2O / acetone View Scheme