Chlorotrimethylsilane → N-(tert-butyl)-N-(trimethylsilyl)benzeneamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1a (0.972 g, 6.51 mmol) in THF (10 mL) was added nBuLi (1.6 M solution in hexanes) (4.3 mL, 6.9 mmol) at −78° C. After 30 min stirring of the reaction mixture at the same temperature, Me3SiCl (0.89 mL, 7.0 mmol) was added at room temperature and the reaction mixture was stirred at 40° C. for 24 h. After evaporating all the volatiles by vacuum, pentane (50 mL) was added. After 20 min stirring of the mixture, stirring was stopped. The supernatant solution was transferred to another flask by a canula. Evaporation of the solvent gave 3a (1.016 g, 70.2%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) 7.32-7.08 (m, 3H), 7.05-6.95 (m, 2H), 1.20 (s, 9H), 0.03 (s, 9H); 13C NMR (75 MHz, CDCl3): δ 148.1, 133.6, 127.9, 124.9, 55.0, 32.1, 4.3. HRMS-ESI (m/z): [M+H]+ calcd for C13H23NSi, 222.1673. found, 222.1670.

Provenance & Evidence