1: (E)-{4-[2-(4-bromophenyl)vinyl]phenyl}dibutylamine With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.333333 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane T=-78°C; 3 h;

1.1: sodium methanolate / dimethylformamide 1.2: 70 percent / dimethylformamide / 12 h 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.33 h / -78 °C 2.2: 71 percent / hexane; tetrahydrofuran / 3 h / -78 °C View Scheme

1.1: 85 percent / 17 h / Heating 2.1: 88 percent / NaH / tetrahydrofuran / 3 h / Heating 3.1: n-BuLi / diethyl ether / -10 °C 3.2: 48 percent / 1 h / -10 °C View Scheme