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

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.

1. addition2.75 mL (30.0 mmol) of borane-dimethyl sulfide complex was added dropwise
2. stirringthe mixture solution was stirred at 0° C. for one hour
3. concentrationThe reaction solution was concentrated
4. customthe residue was partitioned between water and ethyl acetate
5. washthe organic layer was washed with a saturated sodium chloride solution
6. concentrationconcentrated under reduced pressure
7. customThe product was purified by a silica gel column (n-hexane:ethyl acetate=2:1)

ORD record

ord-7405f901763344dd860905541c58157f

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609656B2