1: (Ph3P)4Pd0 / tetrahydrofuran / 24 h / Heating 2: Br2, sodium methoxide / CH2Cl2; methanol / 1.) -78 deg C, 0.5 h, 2.) room temperature, 1 h 3: 1.) tetrakis (triphenylphosphine) palladium, 2.) hydrochloric acid / 1.) THF, reflux, 24 h, 2.) MeOH, room temperature, 3 h View Scheme

1: 95 percent / Pd(PPh3)4 / tetrahydrofuran / 10 h / Heating 2: 85 percent / Br2, NaOMe / CH2Cl2; methanol / 2 h / -78 - 20 °C 3: 84 percent / Pd(PPh3)4 / tetrahydrofuran / 12 h / Heating 4: 93 percent / NaH, C2H5SH / dimethylformamide / 10 h / Heating 5: 60 percent / NaOEt / ethanol / 24 h / Heating View Scheme