Aniline → HCID 68158272, compound

Temperature

-78 °C

To a solution of aniline (1.6 g, 16.9 mmol) in THF (40 mL) at −78° C. was added LiHMDS (34 mL, 1M, 33.9 mmol) and the reaction mixture stirred at −78° C. for 10 min. This solution was added via cannula to a solution of 2,3,4-trifluoronitrobenzene (3 g, 16.9 mmol) in THF (10 mL) at −78° C. and the dark purple reaction mixture stirred at −78° C. for 30 min. The reaction mixture was diluted with water and extracted with EtOAc (3×30 mL). The combined organic fractions were washed with brine, dried (MgSO4), concentrated in vacuo to give the title compound as a dark orange solid (4.2 g, 100%). 1H NMR 400 MHz δ (CDCl3): 8.95 (1H, br s), 8.00 (1H, ddd, J=9.7, 5.4, 2.3 Hz), 7.31-7.25 (2H, m), 7.13-7.08 (1H, m), 7.04-6.99 (2H, m), 6.75-6.67 (1H, m).

1. stirringthe dark purple reaction mixture stirred at −78° C. for 30 min
2. extractionextracted with EtOAc (3×30 mL)
3. washThe combined organic fractions were washed with brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo

ORD record

ord-ad54abe2d8ac4ff4b630f0b5f83b44f3

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653089B2