Pyridine → 4-(1-Chloro-2,2,2-trifluoroethyl)phenol

Temperature

0 °C

To a cooled (ice bath) mixture of 4-(2,2,2-trifluoro-1-hydroxyethyl)phenol (4.3 g, 22 mmol) and anhydrous pyridine (1.8 ml, 22 mmol) in toluene was added thionyl chloride (SOCl2) (2.3 ml, 31 mmol) drop wise via a syringe. After stirred for 1 h at 0° C., the reaction was heated at 70° C. for 2 h. At this point, reaction did not go completion, indicated by LCMS. Heating was continued for 16 h. Reaction was quenched with ice water. The resulted mixture was diluted with EtOAc. The organic layer was washed with saturated Na2CO3, water and brine. After dried over Na2SO4, the solution was filtered and concentrated. The residue was purified on a silica gel column (5-10% EtOAc/hexane) giving the title compound as a light yellow oil. MS m/z: 21 1(M+1).

1. temperatureTo a cooled
2. temperaturethe reaction was heated at 70° C. for 2 h
3. customAt this point, reaction
4. temperatureHeating
5. waitwas continued for 16 h
6. customReaction
7. customwas quenched with ice water
8. additionThe resulted mixture was diluted with EtOAc
9. washThe organic layer was washed with saturated Na2CO3, water and brine
10. dry with materialAfter dried over Na2SO4
11. filtrationthe solution was filtered
12. concentrationconcentrated
13. customThe residue was purified on a silica gel column (5-10% EtOAc/hexane)

ORD record

ord-6a0d75bb118f4e7e9497938f738fd172

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07745484B2