1: ethyl (4-bromophenyl)ethanoate With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 1 h; 2: [(Cyanocarbonyl)oxy]ethane in tetrahydrofuran T=-78 - 20°C;

1: diethyl malonate With N,N,N',N',N'',N''-hexamethylphosphoric triamide; sodium hydride in 1,4-dioxane; mineral oil T=20°C; 1 h; Inert atmosphere; 2: 4-bromo-1-iodobenzene With copper(I) bromide in 1,4-dioxane; mineral oil 5 h; Reflux;

1.1: 94 percent / conc. HCl / Heating 2.1: LHMDS / tetrahydrofuran; hexane / -78 °C 2.2: 66 percent / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

in water; benzene

1: sodium hydride / tetrahydrofuran 2: lithium aluminum hydride / tetrahydrofuran; water View Scheme

1: sodium hydride / tetrahydrofuran 2: lithium aluminum hydride / tetrahydrofuran; water 3: diisopropyl (E)-diazene-1,2-dicarboxylate / toluene View Scheme