Ethanol → 3-Bromo-2-[[(tert-butyldimethylsilyl)oxy]methyl]aniline

Participants

Reaction Conditions

Reaction Steps

A 100-mL three-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 114c (1.00 g, 2.89 mmol), ethanol (20 mL), iron powder (−325 mesh, 1.62 g, 28.9 mmol), ammonium chloride (3.09 g, 57.8 mmol) and water (4 mL), and the reaction mixture was heated at 80° C. for 1 h. After this time, the reaction mixture was cooled to room temperature and filtered through a pad of Celite 521. The filter cake was washed with ethanol (3×50 mL), and the combined filtrates were concentrated under reduced pressure. The resulting residue was triturated with water (10 mL) and then dried to a constant weight at 45° C. under vacuum to afford 114d in quantitative yield (949 mg) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 6.82 (m, 2H), 6.53 (m, 1H), 4.86 (s, 2H), 4.68 (br s, 2H), 0.79 (s, 9H), 0.00 (s, 6H).

Provenance & Evidence