Hydrogen Peroxide → 5-Ethyl-2-fluorophenol

Temperature

-75 °C

A 500 ml THF solution containing 15.5 g of 4-ethylfluorobenzene and 14.6 g of N,N,N′N′-tetramethylethylenediamine was cooled to −75° C. under a nitrogen atmosphere, and then 126 ml of s-butyllithium (0.99 M, cyclohexane solution) was added and the mixture was stirred for 2 hours. Next, 28 ml of trimethyl borate was added, the reaction mixture temperature was raised to room temperature and 14.4 ml of acetic acid was added. After stirring for 30 minutes, the reaction mixture was cooled to 0° C., 28.4 ml of a 30% aqueous solution of hydrogen peroxide was added and stirring was continued at room temperature for 18 hours. Next, 500 ml of a saturated aqueous solution of sodium sulfite was added to the reaction mixture, which was then extracted with 11 of diethyl ether. The organic layer was washed with 500 ml of water and 500 ml of saturated aqueous sodium chloride in that order and dried over anhydrous magnesium sulfate, the desiccant was filtered out, and the filtrate was concentrated under reduced pressure. The residue was distilled to obtain the target compound (16.35 g) as a colorless liquid (boiling point: 76-80° C., 17 mmHg).

1. temperaturethe reaction mixture temperature was raised to room temperature
2. stirringAfter stirring for 30 minutes
3. temperaturethe reaction mixture was cooled to 0° C.
4. stirringstirring
5. waitwas continued at room temperature for 18 hours
6. extractionwas then extracted with 11 of diethyl ether
7. washThe organic layer was washed with 500 ml of water and 500 ml of saturated aqueous sodium chloride in that order
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationthe desiccant was filtered out
10. concentrationthe filtrate was concentrated under reduced pressure
11. distillationThe residue was distilled

ORD record

ord-e2bf90a58e08415eb442d7a234a67685

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807690B2