Hydrogen Peroxide → 2-Fluoro-5-methoxyphenol

To a 200 ml THF solution containing 50.1 g of 1-fluoro-4-methoxybenzene and 70g of N,N,N′,N′,N″-pentamethyldiethylenetriamine there was added dropwise 150 ml of n-butyllithium (2.66 M, hexane solution) over a period of 30 minutes, at −74° C. under a nitrogen atmosphere. After stirring for 3 hours at between −74° C. and −70° C., 100 ml of trimethyl borate was added. The temperature of the reaction mixture was then slowly raised to room temperature. Next, 70 ml of acetic acid and 75 ml of 30% aqueous hydrogen peroxide were added, and the reaction mixture was stirred overnight at room temperature. Water was then added to the reaction mixture, and then it was extracted with a mixture of hexane and ethyl acetate and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure to give a crude product of 1-fluoro-2-hydroxy-4-methoxybenzene (65.59 g) as a white solid.

1. customat −74° C.
2. stirringthe reaction mixture was stirred overnight at room temperature
3. extractionit was extracted with a mixture of hexane and ethyl acetate
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationThe desiccating agent was filtered off
6. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-6974b0504d1e4fdda4cff00a9c7e1492

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928228B2