Imidazole → HCID 58964311, compound

Participants

Reaction Steps

2-Amino-5-chlorophenol (0.949 g, 6.61 mmol), tert-butylchlorodiphenylsilane (2.50 mL, 9.61 mmol), and imidazole (1.335 g, 19.6 mmol) were dissolved in THF (50 mL). Several days later, the reaction mixture was concentrated to give an oil which was purified by SiO2 column chromatography (eluent: 45% dichloromethane/55% hexanes). The product was dried ill vacuo to afford 2-(tert-butyl-diphenyl-silanyloxy)-4-chloro-phenylamine as a yellow oil (784.2 mg, 31%). 1H NMR (400 MHz, DMSO-d6) δ: 7.72-7.64 (m, 4H), 7.55-7.43 (m, 6H), 6.71 (d, J=8.45 Hz, 1H), 6.65 (dd, J=8.46, 2.27 Hz, 1H), 6.10 (d, J=2.26 Hz, 1H), 1.05 (s, 9H).

Provenance & Evidence