Iodine → 2,3,5-Trifluoro-4-iodoaniline

Temperature

20 °C

To a stirred solution of 2,3,5-trifluoro aniline (2.0 g, 13.605 mmol, 1.0 eq) in dry THF (40 mL) at −78° C., was added sec-butyl lithium (10.88 mL, 13.6 mmol, 1.0 eq) over 30 minutes. Stirring was continued at −78° C. for 2 h. A solution of iodine (4.14 g, 16.32 mmol, 1.2 eq) was added dropwise and reaction was slowly warmed to 20° C. over 1 hour (h). The reaction was quenched with 10% aq. Na2S2O3 solution and extracted with methyl tert-butyl ether (MTBE) (3×50 mL). The combined organic extract was washed with saturated (sat.) brine solution, dried over anhydrous Na2SO4, filtered and evaporated to dryness under reduced pressure. The crude product was column purified over silica using 0-10% EtOAc with hexanes as eluent to afford 2,3,5-trifluoro-4-iodoaniline (1.3 g, 35%) as pink solid: 1H NMR (400 MHz, CDCl3) δ 6.43-6.39 (m, 1H), 3.99 (brs, 2H); ESIMS m/z 274 ([M+H]+).

1. customreaction
2. customThe reaction was quenched with 10% aq. Na2S2O3 solution
3. extractionextracted with methyl tert-butyl ether (MTBE) (3×50 mL)
4. extractionThe combined organic extract
5. washwas washed with saturated (sat.) brine solution
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. customevaporated to dryness under reduced pressure
9. custompurified over silica using 0-10% EtOAc with hexanes as eluent

ORD record

ord-48663bfec0e349f6b1141b75bc0f8d93

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09113629B2