Sodium Hydroxide → 5-Amino-2-bromophenol

Temperature

80 °C

4-Bromo-3-methoxyaniline (5.0 g, 25 mmol) was added to 48% hydrobromic acid (20 mL), and the reaction mixture was stirred at 80° C. for 16 hr. After completion of the reaction, the mixture was allowed to cool to room temperature, and adjusted to pH 7-8 by adding 8N aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate, and the obtained organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→100/0) to give the title compound (2.0 g, 43%) as a white powder.

1. customAfter completion of the reaction
2. temperatureto cool to room temperature
3. extractionThe mixture was extracted with ethyl acetate
4. washthe obtained organic layer was washed with water and saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltrated
7. customThe solvent was evaporated under reduced pressure
8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→100/0)

ORD record

ord-d218ad35947245f7b4aab3009bd69fcf

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273741B2