1: 68 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 25 deg C, 12 h 2: 95 percent / trifluoroacetic anhydride, trifluoroacetic acid / 18 h / Ambient temperature 3: 93 percent / dimethylformamide / 18 h / Ambient temperature 4: 1.) hydrogen, 2.) HCl / 1.) 20percent Pd/C / 1.) glacial AcOH, 50 psi, 18 h, 2.) EtOH, 2-propanol 5: BBr3 / 1,2-dichloro-ethane / 1.5 h / Heating View Scheme

1: 68 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 25 deg C, 12 h 2: 95 percent / trifluoroacetic anhydride, trifluoroacetic acid / 18 h / Ambient temperature 3: 93 percent / dimethylformamide / 18 h / Ambient temperature 4: 1.) hydrogen, 2.) HCl / 1.) 20percent Pd/C / 1.) glacial AcOH, 50 psi, 18 h, 2.) EtOH, 2-propanol 5: BBr3 / 1,2-dichloro-ethane / 1.5 h / Heating View Scheme

1: 93 percent / dimethylformamide / 18 h / Ambient temperature 2: 1.) hydrogen, 2.) HCl / 1.) 20percent Pd/C / 1.) glacial AcOH, 50 psi, 18 h, 2.) EtOH, 2-propanol 3: BBr3 / 1,2-dichloro-ethane / 1.5 h / Heating View Scheme

1: 95 percent / trifluoroacetic anhydride, trifluoroacetic acid / 18 h / Ambient temperature 2: 93 percent / dimethylformamide / 18 h / Ambient temperature 3: 1.) hydrogen, 2.) HCl / 1.) 20percent Pd/C / 1.) glacial AcOH, 50 psi, 18 h, 2.) EtOH, 2-propanol 4: BBr3 / 1,2-dichloro-ethane / 1.5 h / Heating View Scheme

1: 83 percent / H2, 5percent Pd-C / methanol; H2O / 25 °C / 2585.7 Torr 2: 1.) BBr3 2.) MeOH / 1.) CH2Cl2, 1,2-dichloroethane, reflux overnight 2.) 4h reflux View Scheme