Hydrogen Peroxide → 4-(2-Hydroxyethyl)-3-(trifluoromethyl)aniline

Participants

Reaction Steps

In 10 mL of anhydrous tetrahydrofuran, 2.47 g (13.2 mmol) of 3-trifluoromethyl-4-vinylaniline was dissolved, and 2.75 mL (30.0 mmol) of borane-dimethyl sulfide complex was added dropwise thereto in an argon atmosphere, and the mixture solution was stirred at room temperature four hours. To the reaction solution, 5 mL of a 1N sodium hydroxyl aqueous solution and 3 mL of a 30% hydrogen peroxide aqueous solution were added and the mixture solution was stirred at 0° C. for one hour. The reaction solution was concentrated and the residue was partitioned between water and ethyl acetate, and the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The product was purified by a silica gel column (n-hexane:ethyl acetate=2:1) to obtain 1.3 g (48%) of a target product as a pale yellow oil.

Provenance & Evidence