Ethyl Acetate → 2-Amino-4-Bromophenol

Participants

Reaction Steps

A solution of KOH (5.14 g, 91.7 mmol) in water (33 mL) was added to 4-bromo-2-nitrophenol (Aldrich, 1.00 g, 4.59 mmol). Sodium hydrosulfite (7.98 g, 45.9 mmol) was added in one portion. The mixture was stirred at RT for 30 min. and poured into ethyl acetate (25 mL). The layers were partitioned and the aqueous layer was extracted with ethyl acetate (4×25 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated to give 488 mg (56%) of the title compound which was used without further purification: 1H NMR (CDCl3, 400 MHz) δ 6.77 (d, 1H, J=2.1 Hz), 6.65 (dd, 1H, J=8.3, 2.5 Hz), 6.52 (d, 1H, J=8.3 Hz); 13C NMR (CDCl3, 100 MHz) δ 144.0, 136.6, 121.7, 118.7, 116.2, 112.1; MS (Cl) m/z 188.0 (M+1); HPLC retention time=1.10 min.

Provenance & Evidence