Hydrogen Peroxide → 5-Ethoxy-2-fluorophenol

To 150 ml of a THF solution containing 10.5 g of 1-ethoxy-4-fluorobenzene, 50 ml of n-butyllithium (1.58 M, hexane solution) was added dropwise at −78° C. under a nitrogen atmosphere. The resulting mixture was stirred for 4 and a half hours, then 8.9 ml of trimethoxy boron was added thereto. Then, the temperature of the mixture was slowly allowed to rise to room temperature. The reaction mixture was stirred for 3 and a half hours, then 12.9 ml of acetic acid and 12.7 ml of a 30% hydrogen peroxide aqueous solution were added thereto at 0° C. The mixture was stirred at room temperature overnight, and then a saturated sodium sulfite aqueous solution was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was crudely purified by silica gel column chromatography (ethyl acetate-heptane) to give a crude product of 5-ethoxy-2-fluorophenol.

1. additionwas added dropwise at −78° C. under a nitrogen atmosphere
2. customto rise to room temperature
3. stirringThe reaction mixture was stirred for 3 and a half hours
4. customat 0° C
5. stirringThe mixture was stirred at room temperature overnight
6. extractionThe mixture was extracted with ethyl acetate
7. washThe organic layer was washed with water and saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. customThe desiccating agent was removed by filtration
10. concentrationthe filtrate was concentrated under reduced pressure
11. customThe residue was crudely purified by silica gel column chromatography (ethyl acetate-heptane)

ORD record

ord-6e9c26d66c1f48aa988ae9b63bf1027d

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07816522B2