Hydrogen Peroxide → 2-Fluoro-5-methoxyphenol

Participants

Reaction Steps

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.

Provenance & Evidence