Potassium Carbonate → 4-(4-Hydroxy-2-methylbutan-2-ylthio)-3-nitrobenzoic acid

To a solution of 4-fluoro-3-nitrobenzoic acid (2 g, 10.80 mmol) in DMF (50 ml) was added potassium carbonate (3.73 g, 27.0 mmol), and 3-mercapto-3-methylbutan-1-ol (1.450 ml, 11.88 mmol). The reaction was stirred at room temperature for 16 hours. The reaction mixture had turned yellow over night. The DMF was removed under reduced pressure and the resulting slurry was diluted with EtOAc (100 mL) and extracted with H2O (100 mL). The aqueous layer was then treated with conc. HCl until a precipitate formed. The mixture was extracted with EtOAc (3×100 mL) and the combined organics were dried over Na2SO4 and concentrated in vacuo. The product was isolated as a yellow solid and used without further purification.

1. waitThe reaction mixture had turned yellow over night
2. customThe DMF was removed under reduced pressure
3. additionthe resulting slurry was diluted with EtOAc (100 mL)
4. extractionextracted with H2O (100 mL)
5. additionThe aqueous layer was then treated with conc. HCl until a precipitate
6. customformed
7. extractionThe mixture was extracted with EtOAc (3×100 mL)
8. dry with materialthe combined organics were dried over Na2SO4
9. concentrationconcentrated in vacuo
10. customThe product was isolated as a yellow solid
11. customused without further purification

ORD record

ord-a148762e4f8a4cd9afab121e5794b810

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960376B2