Ethyl Acetate → 2-Fluoro-4-iodobenzoic acid

2-Fluoro-4-iodo-1-methylbenzene (1.0 g) was added to a solution of potassium permanganate (2.0 g) in water (25 ml). The mixture was gently refluxed for 2 h. Tetrabutylammonium bisulphate (100 mg) was added and the mixture was refluxed for 18h. The cooled solution was treated with ethyl acetate (100 ml) and water (50 ml) and the brown suspension was filtered. The dried organic phase was evaporated and the resulting solid was partitioned between aqueous sodium bicarbonate (2N; 50 ml) and diethyl ether (2×30 ml). The basic solution was acidified with hydrochloric acid (2N) and extracted with dichloromethane (3×50 ml). The dried extract was evaporated to give the title compound as a white solid (120 mg), m.p. 158°-159°.

1. temperatureThe mixture was gently refluxed for 2 h
2. temperaturethe mixture was refluxed for 18h
3. filtrationthe brown suspension was filtered
4. customThe dried organic phase was evaporated
5. customthe resulting solid was partitioned between aqueous sodium bicarbonate (2N; 50 ml) and diethyl ether (2×30 ml)
6. extractionextracted with dichloromethane (3×50 ml)
7. extractionThe dried extract
8. customwas evaporated

ORD record

ord-ea1492470758417cb6fc10dc0a2952e9

Source dataset

uspto-grants-1994_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05358948