Ethanol → 4-Bromo-2-ethoxyaniline

Participants

Reaction Steps

To a refluxing solution of 62A (3.0 g, 12.2 mmol), EtOH (60 mL), water (15 mL) and AcOH (10 mL) was added portion-wise Fe powder (5 g, 89.3 mmol) over 30 min. The mixture was heated for 1 h before cooling to ambient temperature and filtering through celite. The filtrate was concentrated in vacuo to afford 62B (2.5 g, 96%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.42 (t, J=7.03 Hz, 3 H) 4.02 (q, J=6.88 Hz, 2 H) 6.57 (d, J=7.91 Hz, 1 H) 6.85-6.90 (m, 2 H).

Provenance & Evidence