4-Iodoaniline → HCID 86669360, compound

Temperature

-78 °C

To a solution of 4-iodophenylamine (0.940 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 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 triturated with hexane to yield (3-allyloxy-5,6-difluoro-2-nitro-phenyl)-(4-iodo-phenyl)-amine as an orange solid (1.1 g). 1H-NMR (400 MHz, CDCl3): δ 4.54 (2H, d, J=4.8), 5.24 (1H, s), 5.32 (1H, d, J=10.8), 5.42 (1H, d, J=17.2), 6.06-6.02 (1H, m), 6.45 (2H, d, J=8.4), 6.57-6.62 (1H, m), 7.47 (2H, d, J=8.4).

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. concentrationAfter completion, the reaction mixture was concentrated 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-05553c696bdb499ba9aa1a5334da0b97

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034861B2