sodium methylate; tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=100°C;

iodine in methanol 12 h; Heating;

hydrogen bromide; acetic acid T=40°C; 1 h;

potassium carbonate in methanol Heating;

1: oxalyl chloride / CH2Cl2; dimethylformamide / 0 deg C, 1 h; RT, 30 min 2: 84 percent / Et3N / CH2Cl2 / 2 h / Heating 3: 83 percent / 0.33 h / 190 °C / 0.05 Torr 4: 96 percent / sodium methoxide / (PPh3)4Pd / dimethylformamide / 5 h / 100 °C View Scheme

1: 83 percent / 0.33 h / 190 °C / 0.05 Torr 2: 96 percent / sodium methoxide / (PPh3)4Pd / dimethylformamide / 5 h / 100 °C View Scheme

1: 1.) (C2H5)3N / 1.) acetonitrile, room temp 1 h, reflux 5 min, 2.) acetonitrile, reflux, 15 min 2: NaOEt / ethanol / 1.) 10 deg C, 1 h, 2.) room temp, 1 h 3: xylene / 0.5 h / Heating 4: 34 percent / Raney Ni / tetrahydrofuran / 0.17 h / Heating 5: 60 percent / H2, HCl / 10percent Pd-C / ethyl acetate; methanol / 5 h / Ambient temperature 6: 70 percent / 40percent HBr-AcOH / 1 h / 40 °C View Scheme

1: 1.) (C2H5)3N / 1.) acetonitrile, room temp 1 h, reflux 5 min, 2.) acetonitrile, reflux, 15 min 2: NaOEt / ethanol / 1.) 10 deg C, 1 h, 2.) room temp, 1 h 3: xylene / 0.5 h / Heating 4: 34 percent / Raney Ni / tetrahydrofuran / 0.17 h / Heating 5: 60 percent / H2, HCl / 10percent Pd-C / ethyl acetate; methanol / 5 h / Ambient temperature 6: 70 percent / 40percent HBr-AcOH / 1 h / 40 °C View Scheme

1: 60 percent / H2, HCl / 10percent Pd-C / ethyl acetate; methanol / 5 h / Ambient temperature 2: 70 percent / 40percent HBr-AcOH / 1 h / 40 °C View Scheme

1: 34 percent / Raney Ni / tetrahydrofuran / 0.17 h / Heating 2: 60 percent / H2, HCl / 10percent Pd-C / ethyl acetate; methanol / 5 h / Ambient temperature 3: 70 percent / 40percent HBr-AcOH / 1 h / 40 °C View Scheme