sodium hydride in N,N-dimethyl-formamide T=20°C; Smiles rearrangement; 24 h;

1: thionyl chloride / Heating 2: benzene / Heating 3: 47 percent / NaH / dimethylformamide / 24 h / 20 °C View Scheme

1: benzene / Heating 2: 47 percent / NaH / dimethylformamide / 24 h / 20 °C View Scheme

1: 2,4-Dichlorophenylethylamine With n-butyllithium in tetrahydrofuran; hexane T=-45°C; 0.25 h; Inert atmosphere; 2: 1,1'-carbonyldiimidazole in tetrahydrofuran; hexane T=20°C; 16 h; Inert atmosphere;