1: 2-bromo-1-[2-(trimethylsilyl)ethynyl]benzene With n-butyllithium in diethyl ether; hexane T=-78°C; 2.5 h; 2: Et2NMe2SiCl in diethyl ether; hexane T=-78 - 20°C; 3: ethanol With ammonium chloride in diethyl ether; hexane T=20°C; 5 h;

potassium carbonate in tetrahydrofuran; ethanol T=20°C; 22 h;

1: 92 percent / potassium carbonate / tetrahydrofuran; ethanol / 22 h / 20 °C 2: 49 percent / CuI; Et3N / PdCl2(PPh3)2 / tetrahydrofuran / 10 h / 20 °C View Scheme