Chlorotrimethylsilane → N-(trimethylsilyl)-2,4,6-trichloroaniline

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Reaction Conditions

Reaction Steps

Et2O (50 mL) was added to a Schlenk flask under argon containing 2,4,6-trichloroaniline that had been recrystallized from hot hexane. The solution was chilled to −78° C. and n-butyllithium (2.0M in cyclohexane, 4.03 mL, 8.06 mmol) was added via syringe under an argon flow and the resulting white slurry was allowed to stir for 2 h; the slurry acquired a reddish tint over time. Trimethylsilylchloride (1.86 mL, 14.6 mmol) was added by syringe and the solution was allowed to warm to room temperature. Solvent was removed and the orange residue was charged with CH2Cl2. The mixture was filtered over Celite, the Celite washed with CH2Cl2 and the filtrate concentrated under reduced pressure to give an analytically pure orange oil in 90% yield (1.776 g, 6.61 mmol): 1H NMR (C6D6, 20° C.) δ 6.95 (s, 2H, Ar), 3.76 (s, 1H, NH), 0.16 (s, 9H, SiMe3); 13C NMR (C6D6, 20° C.) δ s179.50, 141.26, 124.83, 123.64, 1.783. Anal. Calcd for C9H12Cl3NSi: % C, 40.24; % H, 4.50; N, 5.21. Found: C, 40.01; H, 4.39; N, 5.22.

Provenance & Evidence