Water → 5-Fluoro-2-nitrobenzoic acid

Temperature

100 °C

A mixture of 5-fluoro-2-nitrotoluene (25.0 g, 161 mmol), potassium permanganate (102 g, 645 mmol) and water (500 mL) was heated and stirred at 100° C. for 3 hours. The solution was cooled to room temperature, and insoluble matter derived from potassium permanganate was removed by celite filtration. The filtrate was washed with diethylether, made acidic by the addition of conc. hydrochloric acid, and organic matter was extracted with diethyl ether. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 5-fluoro-2-nitrobenzoic acid. To a solution of 5-fluoro-2-nitro benzoic acid thus obtained in ethanol (100 mL) was added 10% palladium-carbon (0.5 g, 50% hydrate), and the mixture was stirred at room temperature under hydrogen atmosphere for 4 hours. The solution was filtered to remove the catalyst, and the filtrate was concentrated under reduced pressure to give the title compound (6.25 g, 25% yield).

1. temperaturewas heated
2. temperatureThe solution was cooled to room temperature
3. customwas removed by celite filtration
4. washThe filtrate was washed with diethylether
5. additionmade acidic by the addition of conc. hydrochloric acid, and organic matter
6. extractionwas extracted with diethyl ether
7. washThe extract was washed with saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. customthe solvent was evaporated under reduced pressure

ORD record

ord-d9e6544119ad4c6a8f95999580ad2fb5

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06949648B2