Sodium borohydride → 4-(2,2,2-Trifluoro-1-hydroxyethyl)phenol

2,2,2-Trifluoro-1-(4-hydroxy-phenyl)-ethanone (1) (4.1 g, 21.6 mmol) was dissolved in MeOH (50 mL) at 0° C. NaBH4 (1.6 g, 42.2 mmol) was slowly added to the above solution. After 20 minutes, the reaction mixture was quenched with 300 ml of 1M HCl. The mixture thus formed was extracted with ethyl acetate (3×100 mL). The combined organic phases were washed with H2O (3×100 mL), followed by brine (1×200 mL) and then dried over Na2SO4. The organic phase was collected by filtration and concentrated by rotary evaporation to yield a white solid. Recrystallization of the solid with CHCl3 yields intermediate compound (2) as fluffy white crystals (3.14 g, 76%). 1H-NMR (CD3OD): δ 7.28 (d, 2H, J=8.7 Hz), 6.78 (m, 2H), 4.89 (q, 1H, J=7.2 Hz); 19F NMR (CD3OD): δ −80.4 (d, J=7.2 Hz); 13C-NMR (CD3OD): δ 158.0, 128.9, 126.4, 125.2 (q, JCF=280 Hz), 114.9, 71.7 (q, JCF=31 Hz).

1. customthe reaction mixture was quenched with 300 ml of 1M HCl
2. customThe mixture thus formed
3. extractionwas extracted with ethyl acetate (3×100 mL)
4. washThe combined organic phases were washed with H2O (3×100 mL)
5. dry with materialdried over Na2SO4
6. filtrationThe organic phase was collected by filtration
7. concentrationconcentrated by rotary evaporation
8. customto yield a white solid
9. customRecrystallization of the solid with CHCl3

ORD record

ord-3e4a06c1a0664edbbfbc0493bff0e7e4

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09329185B2