N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium 1.) THF, -90 deg C,; Yield given. Multistep reaction;

N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium 1.) THF, -78 deg C, 2.) -78 deg C; Yield given. Multistep reaction;

1: 1.) LDA / THF, 1.) -78 deg C, 1 h ; 2.) a. -78 deg C , 4 h , b. room temperature , 4 h 2: 50percent NaOH / H2O; ethanol / 8 h / Heating 3: 94 percent / BBr3 / CH2Cl2 / 1.) -78 deg C , 1 h , 2.) -78 deg C to RT , 12 h View Scheme

1: 1.) LDA / THF, 1.) -78 deg C, 1 h ; 2.) a. -78 deg C , 4 h , b. room temperature , 4 h 2: 50percent NaOH / H2O; ethanol / 8 h / Heating 3: 30 percent / AlCl3 / nitrobenzene / 1 h / 80 °C View Scheme