2,2,2-Trifluoro-N-phenylacetamide → Aniline, N-(2,2,2-trifluoroethyl)-

To a solution of 2,2,2-trifluoro-N-phenylacetamide (5.0 g, 26 mmol) in THF (10 mL) was added BH3 in THF (130 mL, 130 mmol, 1.0 M). The resulting mixture was refluxed overnight. The mixture was quenched with water and methanol, concentrated to remove most of THF, and extracted with EtOAc. Organics were washed with brine, dried (Na2SO4), and concentrated to give 4.17 g (92%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 3.71-3.75 (2H, m), 6.66 (2H, d, J=8.0 Hz), 6.79 (1H, t, J=7.2 Hz), 7.20 (2H, t, J=8.0 Hz).

1. temperatureThe resulting mixture was refluxed overnight
2. customThe mixture was quenched with water and methanol
3. concentrationconcentrated
4. customto remove most of THF
5. extractionextracted with EtOAc
6. washOrganics were washed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated

ORD record

ord-5dbcc5a4847a4c849cb9ac0248c9d91c

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447046B2