Chlorotrimethylsilane → N-(trimethylsilyl)-2,6-dichloro-4-trifluoromethylaniline

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Reaction Conditions

Reaction Steps

Et2O (200 mL) was added to a Schlenk flask under nitrogen containing 2,6-dichloro-4-trifluoromethylaniline (14.39 g, 62.6 mmol) and was cooled to −78° C. n-butyllithium (2.5M in hexane, 26.3 mL, 65.7 mmol) was added over 15 min to the stirred solution. The solution was stirred at −78° C. for 2 h and was then taken out of the cold bath, during which time a dark red/brown color evolved. Trimethylsilyl chloride (15.9 mL, 125 mmol) was then added dropwise to afford a light yellow slurry. This mixture was allowed to warm to room temperature and was filtered through Celite. The yellow filtrate was concentrated under reduced pressure to give an analytically pure orange oil; yield 18.90 g, (98%): 1H NMR (C6D6, 20° C.) δ 7.24 (s, 2H, Ar), 4.21 (bs, 1H, NH), 0.16 (s, 9H, TMS); 13C NMR (C6D6, 20° C.) δ 145.68, 125.4 (m), 123.90 (q, 1JCF=271 Hz), 123.44, 121.29 (q, 2JCF=33.8 Hz), 2.23 (m); 19F NMR (C6D6, 20° C.) δ −61.77. Anal. Calcd for C10H12Cl2F3NSi: C, 39.75; H, 4.00; N, 4.64. Found: C, 40.06; H, 3.84; N, 4.42.

Provenance & Evidence