diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide in tetrahydrofuran Sonogashira coupling;

1: 1-chloro-4-iodobenzene With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine T=20°C; 0.0833333 h; 2: C8H12O3 With diethylamine T=20°C; 2 h;

1.1: aq. KOH / methanol / 12 h 2.1: 1.26 g / [2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium]*BF4; (i-Pr)2NEt / CH2Cl2 / 12 h 3.1: BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C 3.2: 62 percent / hexane; tetrahydrofuran / -78 - 20 °C View Scheme