Bromine → HCID 49766558, compound

Participants

Reaction Steps

To a solution of 2-amino-5-nitro-phenol (500 g, 3.24 mol) in ACN (12 L) was added bromine (290 mL, 5.63 mol) drop wise over a period of 30 min under stirring. The resulting mixture was stirred at 30-35° C. for 1 h. After the completion of the reaction (by TLC), solvent was evaporated till dryness. Hexane was added (2 L) and the mixture evaporated to remove solvent traces. Hexane (5 L) was added again to the residue and the mixture stirred for 1 h then filtered. The resulting solid (1102 g) was washed with hexane (2 L). The residue was added to ice-cold water (2.5 L) followed by addition of a saturated solution of sodium thiosulfate (2.5 L) and extraction with EtOAc (2×10 L). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated at 40-45° C. under reduced pressure to obtain the desired product (643 g crude yield 85%).

Provenance & Evidence