Methanol → 2,2,2-Trifluoro-1-(4-mercapto-phenyl)-ethanol

In a 2-neck round bottom flask, NaOH (330 mg, 5.5 mmol) and dimethyl-thiocarbamic acid S-[4-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenyl]ester (4) (16 mg, 0.59 mmol) was dissolved in THF (5 mL) and MeOH (0.82 mL) under argon at 69° C. After 3 hours, the reaction mixture was quenched under argon with 1M HCl (3 mL) and was extracted with ethyl acetate (3×30 mL). The combined organic phases were washed with H2O (3×30 mL), followed by brine (1×30 mL), and then dried over Na2SO4. The organic phase was collected by filtration and concentrated by rotary evaporation to yield intermediate compound (5) as a yellow oil (107 mg, 65%). 1H NMR (400 MHz, CHCl3): δ 7.53 (m, 2H), 7.43 (d, J=8.68, 2H), 5.01 (q, J=6.55, 1H); 19F NMR (376 MHz, CDCl3): −79 (d, J=6.7 Hz); 13C NMR (100 MHz, CDCl3): δ 133.2, 131.5, 129.3, 128.4, 124.4 (q, JCF=282.1 Hz), 72.5 (q, JCF=32 Hz).

1. customat 69° C
2. customthe reaction mixture was quenched under argon with 1M HCl (3 mL)
3. extractionwas extracted with ethyl acetate (3×30 mL)
4. washThe combined organic phases were washed with H2O (3×30 mL)
5. dry with materialdried over Na2SO4
6. filtrationThe organic phase was collected by filtration
7. concentrationconcentrated by rotary evaporation

ORD record

ord-c23bba24658148329cbbeb66b6542520

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09329185B2