Acetanilide → 3-Fluorodiphenylamine

Temperature

180 °C

In a round bottom flask equipped with a condenser was placed N-phenylacetamide (1.0 g, 7.40 mmol), copper (I) chloride (0.146 g, 1.480 mmol), potassium carbonate (1.329 g, 9.62 mmol), 1-bromo-3-fluorobenzene (1.942 g, 11.10 mmol) and xylene (5 mL). The suspension was heated to 180° C. and refluxed for 66 h. The suspension was filtered; and the filtrate was concentrated. The dark brown residue was dissolved in ether; filtered; and the filtrate was concentrated. The dark brown residue was dissolved in ethanol (10.00 mL), treated with potassium hydroxide (1.909 g, 34.0 mmol) and refluxed for 2 h. The solution was poured into of water (80 mL) and extracted with DCM. The combined DCM extract was washed with water (6 X), dried over MgSO4 and concentrated to afford the title compound as a dark brown solid (0.669 g,). LCMS m/z=188.2 [M+H]+.

1. customIn a round bottom flask equipped with a condenser
2. temperaturerefluxed for 66 h
3. filtrationThe suspension was filtered
4. concentrationand the filtrate was concentrated
5. dissolutionThe dark brown residue was dissolved in ether
6. filtrationfiltered
7. concentrationand the filtrate was concentrated
8. dissolutionThe dark brown residue was dissolved in ethanol (10.00 mL)
9. temperaturerefluxed for 2 h
10. extractionextracted with DCM
11. extractionThe combined DCM extract
12. washwas washed with water (6 X)
13. dry with materialdried over MgSO4
14. concentrationconcentrated

ORD record

ord-23a1e1443da041ed9825e973415eec12

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895776B2