2-amino-3-bromo-5-nitrophenol synthesis

Yield:915156-09-1 92%

Reaction Conditions:

with bromine in dichloromethane at 0 - 20; for 0.75 h;

Steps:

18.1

2-Amino-3-bromo-5-nitro-phenolTo an ice-cold solution of 2-amino-5-nitro phenol (40.0 g, 259.52 mmol) in DCM (1.0 L), was added bromine (13.38 mL, 259.52 mmol) drop wise. The resulting reaction mixture was stirred at room temperature for 45 min. After the completion of the reaction (TLC monitoring), water was added and extracted with EtOAc (3 x 1.0 L). The combined organics was dried over anhydrous Na₂SO₄ and concentrated under reduced pressure. The crude (55.0 g, 92%) was carried forward to the next step without further purification.¹H-NMR (400 MHz, DMSO-d₆): δ 6.06 (s, 2H), 7.48 (s, 1 H), 7.85 (s, 1 H) and 10.68 (s, 1 H).

References:

WO2007/148093,2007,A1 Location in patent:Page/Page column 76-77