1-Nitro-4-(2,2,2-trifluoroethoxy)benzene → 4-(2,2,2-Trifluoroethoxy)aniline

To a solution of the crude 4-(2,2,2-trifluoroethoxy)nitrobenzene (1.6 g, 7.2 mmol, 1.0 equiv) in 40 mL of dichloromethane was added 0.4 g of a 5% palladium on activated carbon (0.19 mmol, 0.026 equiv). Hydrogen gas was introduced using a balloon while the mixture was stirred vigorously for 48 h at room temperature. After all starting material had been consumed, the mixture was filtered through a pad of Celite to remove the palladium catalyst. The filtrate was evaporated in vacuo to give a crude product as a brown liquid. This crude product was purified by distillation at reduced pressure to give 1.3 g of pure 4-(2,2,2-trifluoroethoxy)aniline as a colorless liquid, which solidified upon cooling to 0° C. b.p. 81-83° C. at 0.5 torr;. 1H NMR (DMSO-d6) δ4.53 (q, J=9.1 Hz, 2H), 4.76 (br s, 2H), 6.52 (d, J=7.6 Hz, 2H), 6.76 (d, J=7.6 Hz, 2H) ppm.

1. customAfter all starting material had been consumed
2. filtrationthe mixture was filtered through a pad of Celite
3. customto remove the palladium catalyst
4. customThe filtrate was evaporated in vacuo
5. customto give a crude product as a brown liquid
6. distillationThis crude product was purified by distillation at reduced pressure

ORD record

ord-f2f2067868714495bcec81c6e4e141e1

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06794379B2