2-Fluoro-4-iodoaniline → HCID 86669357, compound

Temperature

-78 °C

To a solution of 2-fluoro-4-iodo-phenylamine (1.1 g, 4.6 mmol) in THF (50 mL) was dropwise added LHMDS solution (6.0 mL, 6.0 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-nitrobenzene (1.2 g, 5.1 mmol) in THF (10 mL) was dropwise added into the reaction mixture. The reaction mixture was stirred at −78° C. for additional 1 h and brought to room temperature and stirred for 16 h. The progress of reaction was monitored by 1H NMR. After completion, the solvent was removed under reduced pressure. The residue obtained was dissolved in ethyl acetate, washed with water, dried over anhydrous Na2SO4 and concentrated. The residue was triturated with hexane to yield (3-allyloxy-5,6-difluoro-2-nitro-phenyl)-(2-fluoro-4-iodo-phenyl)-amine as a yellow solid (900 mg). 1H-NMR (400 MHz, CDCl3): δ 4.62 (2H, d, J=4.8), 5.33-5.36 (1H, d, J=10), 5.48 (1H, d, J=17.2), 5.98-6.02 (1H, m), 6.22 (1H, dd, J=2.4, 9.6), 6.36 (1H, dd, J=2, 10.4), 7.04-7.08 (1H, m), 7.45-7.52 (2H, m), 7.79 (1H, s).

1. customat −78° C
2. stirringThe reaction mixture was stirred at −78° C. for additional 1 h
3. custombrought to room temperature
4. stirringstirred for 16 h
5. customThe progress of reaction
6. customAfter completion, the solvent was removed under reduced pressure
7. customThe residue obtained
8. washwashed with water
9. dry with materialdried over anhydrous Na2SO4
10. concentrationconcentrated
11. customThe residue was triturated with hexane

ORD record

ord-aba3a2a998e84e5297a88e9faf4ae310

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034861B2