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

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

1. additiondimethyl sulfide complex (2.75 mL, 30.0 mmol) was dropwise added
2. stirringThe resulting mixture was stirred at 0° C. for 1 hour
3. concentrationThe reaction solution was concentrated
4. customthe residue was partitioned between water and ethyl acetate
5. washThe organic layer was washed with saturated brine
6. concentrationconcentrated under reduced pressure
7. customThe resulting product was purified by silica-gel column chromatography (n-hexane:ethyl acetate=2:1)

ORD 기록

ord-3230b52f61c24c22ae98b945e933577f

출처 데이터셋

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08299252B2