1: 1-(iodo)-4-methylbenzene With copper(l) iodide; 1,10-phenanthroline; potassium hydroxide in water; dimethyl sulfoxide T=20 - 100°C; Inert atmosphere; 2: 1-bromo-octane With tetra-(n-butyl)ammonium iodide; potassium hydroxide in water; dimethyl sulfoxide T=20 - 100°C; Inert atmosphere;

1: para-bromotoluene With copper(l) iodide; 2-methyl-8-hydroxyquinoline; tetra(n-butyl)ammonium hydroxide in water; dimethyl sulfoxide T=130°C; 2: 1-bromo-octane With tetra(n-butyl)ammonium hydroxide in water; dimethyl sulfoxide T=100°C; Williamson reaction;

potassium hydroxide in N,N-dimethyl-formamide 1 h; Heating;

sodium Yield given. Multistep reaction;

potassium hydroxide