triethylamine; bis-triphenylphosphine-palladium(II) chloride in N,N-dimethyl-formamide T=110°C;

titanium tetrachloride in dichloromethane T=20°C; 2 h;

1: 4-bromo-7-methoxy-2-phenyl-benzofuran With n-butyllithium in tetrahydrofuran; hexane T=-90°C; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane T=20°C;

1.1: 92 percent / NaBH4 / methanol / 1 h / 20 °C 2.1: 95 percent / aq. HBr / acetonitrile / 3 h / Heating 3.1: Et3N / toluene / Heating 4.1: n-BuLi / tetrahydrofuran; hexane / -90 °C 4.2: tetrahydrofuran; hexane / 20 °C View Scheme

1.1: 95 percent / aq. HBr / acetonitrile / 3 h / Heating 2.1: Et3N / toluene / Heating 3.1: n-BuLi / tetrahydrofuran; hexane / -90 °C 3.2: tetrahydrofuran; hexane / 20 °C View Scheme