Chlorotrimethylsilane → HCID 53962653, compound

Participants

Reaction Steps

TMSCl (8.5 g, 78.24 mmol) and tert-butyl (2,6-di-tert-butylphenyl) carbonate (12.0 g, 39.16 mmol) was added to a suspension of KNO3 (5.9 g, 58.36 mmol) in CHCl3 (100 mL) successively at 0° C. The reaction mixture was stirred for 0.5 h and AlCl3 (15.5 g, 116.20 mmol) was added. The stirring was continued for 2 h and the resulting mixture was poured into ice-water and extracted with CH2Cl2. The combined organic layers were washed with sat. NaHCO3 solution and brine, dried over Na2SO4 and evaporated in vacuo. The crude product was purified by silica gel column chromatography (petroleum ether) to give 2,6-di-tert-butyl-3-nitrophenol (2.5 g, 25%). 1H NMR (300 MHz, CDCl3) δ 7.18 (d, J=8.4 Hz, 1H), 6.79 (d, J=8.4 Hz, 1H), 5.57 (s, 1H), 1.51 (s, 9H), 1.44 (s, 9H).

Provenance & Evidence