1,2,3,5-Tetrafluoro-4-nitrobenzene → 2,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitroaniline

Temperature

-78 °C

To a solution of 2-fluoro-4-iodoaniline (1.0 g, 4.21 mmol) in THF (20 mL) was dropwise added LHMDS solution (5.1 mL, 5.1 mmol, 1 M in THF) at −78° C. After stirring at −78° C. for 30 min, a solution of 2,3,4,6-tetrafluoronitrobenzene (0.823 g, 4.21 mmol) in THF (5 mL) was added drop wise into the reaction mixture, which was slowly warmed to room temperature and stirred for 16 h. After completion (as indicated by TLC), the reaction mixture was quenched with water and extracted with ether. The organic layer was dried over anhydrous Na2SO4 and concentrated. The crude residue was triturated with hexane to yield 2,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitrobenzenamine (0.748 g). 1H-NMR (400 MHz, CDCl3): δ 6.71-6.76 (2H, m), 7.40 (1H, d, J=8.8), 7.46 (1H, d, J=10), 7.69 (1H, s).

1. customat −78° C
2. temperaturewas slowly warmed to room temperature
3. stirringstirred for 16 h
4. customAfter completion (as indicated by TLC), the reaction mixture was quenched with water
5. extractionextracted with ether
6. dry with materialThe organic layer was dried over anhydrous Na2SO4
7. concentrationconcentrated
8. customThe crude residue was triturated with hexane

ORD record

ord-19630a74f00b4002a72ff9bd650772d3

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034861B2