Formic Acid → 2-Fluoro-4-sulfamoylbenzoic acid

To a stirred solution of 3-fluoro-4-methyl-benzenesulfonamide (prepared above) in 50 mL of water was added sodium carbonate (0.53 g, 5 mmol) and potassium permanganate (3.16 g, 20 mmol) portionwise over three hours at 50˜60° C. The resulting mixture was stirred for further 8 hours at this temperature before 0.2 mL of formic acid was added to quench the excess of potassium permanganate. The mixture was then filtered through celite while it was still hot and further washed with the hot water. The filtrate was concentrated to ˜30 mL and adjusted to pH 9˜10. The filtration was applied again to remove non-oxidized starting material. The final filtrate was acidified with HCl (conc.) to ˜pH 1 and 4-(aminosulfonyl)-2-fluorobenzoic acid was precipitated and collected by filtration as white solid (1.10 g, 50%).

1. additionwas added
2. customto quench the excess of potassium permanganate
3. filtrationThe mixture was then filtered through celite while it
4. washfurther washed with the hot water
5. concentrationThe filtrate was concentrated to ˜30 mL
6. filtrationThe filtration
7. customto remove non-oxidized
8. customwas precipitated
9. filtrationcollected by filtration as white solid (1.10 g, 50%)

ORD record

ord-8e653d35cea14be2b08c99ef74ca0a62

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07645771B2