Water → 2-Fluoro-4-iodobenzoic acid

Temperature

70 °C

13.39 g (84.74 mmol) potassium permanganate were added to a suspension of 5 g (21.18 mmol) of 2-fluoro-4-iodo-toluene and 25.13 g (317.77 mmol) of pyridin in water. The mixture was heated and stirred at 70° C. during 18 hours. As the reaction was not finished, 3.34 g (21.18 mmol) of potassium permanganate were added to the reaction mixture at room temperature and the mixture was stirred for another 6 hours at 70° C. The reaction mixture was then filtered through a celite pad, which was then washed with water and ethyl acetate. After decantation, the aqueous phase was acidified to pH=1 with an aqueous solution of HCl 6N. A white solid was first filtered and the aqueous phase extracted three times with ethyl acetate. The combined organic phases were dried over MgSO4 and the solvents were evaporated off under reduced pressure. The filtered white solid and the solid extracted with ethyl acetate were combined to give 4.1 g.

1. temperatureThe mixture was heated
2. stirringthe mixture was stirred for another 6 hours at 70° C
3. filtrationThe reaction mixture was then filtered through a celite pad, which
4. washwas then washed with water and ethyl acetate
5. filtrationA white solid was first filtered
6. extractionthe aqueous phase extracted three times with ethyl acetate
7. dry with materialThe combined organic phases were dried over MgSO4
8. customthe solvents were evaporated off under reduced pressure
9. extractionThe filtered white solid and the solid extracted with ethyl acetate
10. customto give 4.1 g

ORD record

ord-19f60886038e4fabb1be91b0282509ea

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09126972B2