Ethanol → 4-Fluoro-3,3-dimethyl-2-oxobutanoic acid

To a vigorous stirring mixture of 4-fluoro-3,3-dimethylbutan-2-one (4.1 g, 34.7 mmol) in water (50 mL) and NaOH (7 mL, 70.0 mmol) cooled in an ice-acetone bath was added portionwise potassium permanganate (9.87 g, 62.5 mmol). The inner temperature was controlled between −3 to 2° C. during the addition process. Upon the completion of the addition, the reaction mixture was stirred in the ice-acetone bath for 6 hrs and then allowed to warm up. EtOH (5 mL) was added and the reaction mixture was stirred for another 15 min. The reaction mixture was filtered and the solid was washed with water (˜80 mL). The filtration was acidified with 6 N HCl, and extracted with EtOAc. The combined extracts were washed with 1N HCl, sat. NaCl, dried (Na2SO4), filtered and concentrated to yield 4-fluoro-3,3-dimethyl-2-oxobutanoic acid (2.3 g).

1. temperaturecooled in an ice-acetone bath
2. customwas controlled between −3 to 2° C. during the addition process
3. additionUpon the completion of the addition
4. temperatureto warm up
5. filtrationThe reaction mixture was filtered
6. washthe solid was washed with water (˜80 mL)
7. filtrationThe filtration
8. extractionextracted with EtOAc
9. washThe combined extracts were washed with 1N HCl, sat. NaCl
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. concentrationconcentrated

ORD-Eintrag

ord-add77a6f154e4496915beb8231a3899d

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09326973B2