Ethylamine → 5-Bromo-N-ethyl-2-nitroaniline

Temperature

50 °C

The mixture of 4-bromo-2-fluoro-1-nitrobenzene (5 g) and ethylamine (2 M in THF, 17.05 ml) was stirred at room temperature for 2 h and at 50° C. for 2 h. After concentration of the mixture, the residue was quenched with saturated NaHCO3 solution at room temperature and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The progress of the reaction was followed by NMR, but 4-bromo-2-fluoro-1-nitrobenzene was remained. The resulting residue was dissolved in EtOH (25 ml), and heated with potassium carbonate (6.28 g) and ethylamine (15.6 M in water, 1.47 ml) at 50° C. for 2 h. The resulting suspension was filtered. The precipitate was washed with EtOH and water and dried to give the title compound (4.45 g) as a pale yellow solid.

1. customAfter concentration of the mixture, the residue was quenched with saturated NaHCO3 solution at room temperature
2. extractionextracted with EtOAc
3. customThe organic layer was separated
4. washwashed with water and brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. dissolutionThe resulting residue was dissolved in EtOH (25 ml)
8. temperatureheated with potassium carbonate (6.28 g) and ethylamine (15.6 M in water, 1.47 ml) at 50° C. for 2 h
9. filtrationThe resulting suspension was filtered
10. washThe precipitate was washed with EtOH and water
11. customdried

ORD record

ord-64c9beb6a1a1497b95aa3264add25795

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365540B2