1,2,3,5-Tetrafluoro-4-nitrobenzene → HCID 86669362, compound

Temperature

-78 °C

To a solution of 4-bromo-2-fluoro-phenylamine (2.0 g, 10.5 mmol) in THF (80 mL) was dropwise added LHMDS solution (12.6 mL, 12.6 mmol, 1 M in THF) at −78° C. After stirring at −78° C. for 1 h, a solution of 1,2,3,5-tetrafluoro-4-nitro-benzene (2.05 g, 10.5 mmol) in THF (20 mL) was added dropwise into the reaction mixture, which was stirred at −78° C. for 1 h, and at room temperature for 16 h. The progress of reaction was monitored by 1H NMR. After completion, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried over anhydrous Na2SO4 and concentrated. The residue obtained was re-crystallized in hexane to yield (4-bromo-2-fluoro-phenyl)-(2,3,5-trifluoro-6-nitro-phenyl)-amine as a yellow solid (1.6 g). 1H-NMR (400 MHz, CDCl3): δ 6.73-6.75 (1H, m), 6.86-6.87 (1H, m), 7.22 (1H, d, J=8.4), 7.30 (1H, dd, J=2.0 Hz, 10.8), 7.71 (1H, s).

1. customat −78° C
2. stirringwas stirred at −78° C. for 1 h
3. waitat room temperature for 16 h
4. customThe progress of reaction
5. concentrationAfter completion, the reaction mixture was concentrated under reduced pressure
6. dissolutionThe residue was dissolved in ethyl acetate
7. washwashed with water
8. dry with materialdried over anhydrous Na2SO4
9. concentrationconcentrated
10. customThe residue obtained
11. customwas re-crystallized in hexane

ORD record

ord-1f12b0c981c24e369e76e41153f90cba

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034861B2