2-Fluoroaniline → HCID 68157911, compound

Temperature

-70 °C

A solution of 2-fluorophenylamine (1.47 g, 13.19 mmol) in anhydrous THF (20 mL) was cooled to −70° C. To this was added dropwise 1M LiHMDS in THF (25.14 mL, 25.14 mmol) over 10 minutes to afford a dark yellow solution. A solution of 2,4-difluoronitrobenzene (2.00 g, 12.57 mmol) in anhydrous THF (10 mL) was added dropwise to the yellow solution, to afford a purple solution. The was stirred at −70° C. for 15 minutes, before being allowed to reach RT. It was then quenched with saturated aqueous NH4Cl solution (25 mL) and extracted into EtOAc (3×50 mL). The combined organic fractions were washed with brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo to afford an orange solid. This was purified by column chromatography (silica gel, gradient 0-100% DCM in cyclohexane) to afford the title compound as a yellow solid (3.04 g, 97%). 1H NMR (CDCl3, 400 MHz): δ 9.36 (1H, s), 8.20 (1H, dd, J=9.45, 5.94 Hz), 7.34-7.26 (1H, m), 7.24-7.10 (3H, m), 6.56 (1H, dt, J=11.09, 2.07 Hz), 6.45 (1H, ddd, J=9.44, 7.13, 2.63 Hz)

1. customto afford a dark yellow solution
2. customto afford a purple solution
3. customto reach RT
4. customIt was then quenched with saturated aqueous NH4Cl solution (25 mL)
5. extractionextracted into EtOAc (3×50 mL)
6. washThe combined organic fractions were washed with brine (25 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto afford an orange solid
11. customThis was purified by column chromatography (silica gel, gradient 0-100% DCM in cyclohexane)

ORD record

ord-d0fa1b3f8167471284def3647cbb332d

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653089B2