Acetic Anhydride → N-(3-Fluoro-4-trifluoromethyl-phenyl)-acetamide

Temperature

23 °C

To a mixture of 3-fluoro-4-trifluoromethyl-phenylamine (16.9 g, 92.6 mmol), N,N-dimethyl-4-aminopyridine (1.13 g, 9.26 mmol), and toluene (230 mL) was added acetic anhydride (13.1 mL, 0.139 mol). The reaction mixture was heated at reflux for 3 h, and stirred at 23° C. for 16 h. The reaction mixture was concentrated and the crude product was dissolved in EtOAc (100 mL). The organic layer was washed with water (40 mL) and brine (40 mL), dried, filtered, and concentrated under reduced pressure. The crude solid was triturated from DCM/hexanes to yield the titled compound (16.5 g, 81% yield). MS (ESI/CI): mass calcd. for C9H7F4NO, 221.1; m/z found, 222.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.68 (d, J=12.5 Hz, 1H), 7.52 (t, J=8.3 Hz, 1H), 7.45 (br s, 1H), 7.19 (d, J=8.5 Hz, 1H), 2.22 (s, 3H).

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 3 h
3. concentrationThe reaction mixture was concentrated
4. dissolutionthe crude product was dissolved in EtOAc (100 mL)
5. washThe organic layer was washed with water (40 mL) and brine (40 mL)
6. customdried
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude solid was triturated from DCM/hexanes

ORD record

ord-80cdcea9db7d4e55870b3cc651c88531

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073923B2