Hydrogen Peroxide → 5-Ethyl-2-fluorophenol

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence