Hydrogen Peroxide → 2-Fluoro-5-methoxyphenol

To a 200 ml THF solution containing 50.1 g of 1-fluoro-4-methoxybenzene and 70 g of N,N,N′,N′,N″-pentamethyldiethylenetriamine there was added dropwise 150 ml of n-butyllithium (2.66 M, hexane solution) at −74° C. over a period of 30 minutes, under a nitrogen atmosphere. After stirring between −74° C. and −70° C. for 3 hours, 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 a 30% hydrogen peroxide aqueous solution were added and the reaction mixture was stirred overnight at room temperature. After the addition of water to the reaction mixture, it was extracted with a hexane/ethyl acetate mixture and dried over anhydrous magnesium sulfate. The desiccant was filtered out, and the filtrate was concentrated under reduced pressure to obtain a crude product of 1-fluoro-2-hydroxy-4-methoxybenzene (65.59 g) as a colorless solid.

1. stirringthe reaction mixture was stirred overnight at room temperature
2. extractionwas extracted with a hexane/ethyl acetate mixture
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationThe desiccant was filtered out
5. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-3b80f9099ff945dfa6158cb04b9db81a

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07807690B2