1: 2-bromo-N-(prop-2-enyl)aniline With tert.-butyl lithium in diethyl ether; n-heptane T=-78°C; 1 h; 2: With N,N,N',N,-tetramethylethylenediamine in diethyl ether; n-heptane T=5°C; 2 h; 3: tert-butyldimethylsilyl chloride; allyl bromide in diethyl ether; n-heptane T=20°C; 1 h;

1.1: MeMgBr / tetrahydrofuran 1.2: 64 percent / toluene / Heating 2.1: tert-butyllithium / diethyl ether; heptane / 1 h / -78 °C 2.2: TMEDA / diethyl ether; heptane / 2 h / 5 °C 2.3: 64 percent / diethyl ether; heptane / 1 h / 20 °C View Scheme

N,N,N',N,-tetramethylethylenediamine; tert.-butyl lithium 1.) n-C5H12, Et2O, -78 deg C, 2.) 0 deg C, 40 min; Yield given. Multistep reaction;