(Diethylamino)sulfur trifluoride → 2-(Trifluoromethoxy)fluorobenzene

Dimethoxyethane (15 ml) was added to the above 3-(4-(2-(3-fluoro-4-trifluoromethoxyphenyl)ethyl)cyclohexyl)propanol (1.52 g, 4.4 mmol), followed by-dropwise adding DAST (1.40 g, 8.7 mmol), refluxing the mixture for 5 hours, extracting the resulting product with toluene, washing the organic layer successively with a saturated aqueous solution of sodium bicarbonate and water, drying over MgSO4, distilling off the solvent, purifying the residue according to column chromatography treatment using heptane as a developing solvent, on silica gel, distilling off the solvent, and recrystallizing the residue from ethanol, to isolate 1-(3-fluoropropyl)cyclohexyl)-3-fluoro-4-trifluoromethoxybenzene (0.12 g, 0.34 mmol). Yield: 7.7%. Its clearing point measured by PERKIN-ELMER 7 series Thermal Analysis System was -5.89° C.

1. temperaturerefluxing the mixture for 5 hours
2. extractionextracting the resulting product with toluene
3. washwashing the organic layer successively with a saturated aqueous solution of sodium bicarbonate and water
4. dry with materialdrying over MgSO4
5. distillationdistilling off the solvent
6. custompurifying the residue
7. distillationon silica gel, distilling off the solvent
8. customrecrystallizing the residue from ethanol

ORD record

ord-02eb0efdbb7a44198ae37bb13d50d3c4

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05702641