Imidazole → 2-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4-chloroaniline

Participants

Reaction Steps

To a stirred solution of 2-amino-5-chlorophenylmethanol (11.1 g, 70.4 mmol) in tetrahydrofuran (50 mL) was added imidazole (5.27 g, 77.5 mmol), followed by careful addition of tert-butyldimethylchlorosilane (10.62 g 70.4 mmol). The reaction mixture was stirred for 24 hours. Imidazole (528 mg, 7.75 mmol) and tert-butyldimethylchlorosilane (1.06 g, 7.03 mmol) were then added. After 1 hour the solid was filtered off and washed with diethyl ether (2×20 mL) and the filtrate was washed with water (10 mL), brine (10 mL), dried over magnesium sulfate and concentrated in vacuo to give the product as a brown oil, 18.83 g (98%).

Provenance & Evidence