4-Bromo-2-fluoroaniline → HCID 86669359, compound

Temperature

-78 °C

To a solution of 4-bromo-2-fluoro-phenylamine (0.815 g, 4.3 mmol) in THF (50 mL) was dropwise added LHMDS solution (5.6 mL, 5.6 mmol, 1 M in THF) at −78° C. After stirring for 1 h at −78° C., a solution of 1-allyloxy-3,4,5-trifluoro-2-nitro-benzene (1.1 g, 4.7 mmol) in THF (10 mL) was dropwise added 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 solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried over anhydrous Na2SO4 and concentrated. The residue obtained was triturated with hexane to yield (3-allyloxy-5,6-difluoro-2-nitro-phenyl)-(4-bromo-2-fluoro-phenyl)-amine as a yellow solid (724 mg). 1H-NMR (400 MHz, CDCl3): δ 4.55 (2H, d, J=5.6), 5.32-5.36 (2H, m), 5.42 (1H, d), 6.02-6.08 (1H, m), 6.35 (1H, t, J=8.8), 6.60-6.65 (1H, m), 7.06 (1H, d, J=8.4), 7.23 (1H, dd, J=2.0, 10.4).

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

ORD record

ord-ea9f87a6a05e4a77b3e823af865bc539

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034861B2