4-Fluorothiophenol → (2,2-Dimethoxyethyl)(4-fluorophenyl)sulfane

In a nitrogen stream, 4-fluorobenzenethiol (2.5 ml, 23.4 mmol) and 2-bromo-1,1-dimethoxyethane (3.0 ml, 25.7 mmol) were added to a sodium methoxide methanol solution (0.5 M, 74.9 ml, 37.4 mmol) under cooling with ice and the reaction mixture was stirred at the same temperature for 10 minutes, and then heated and refluxed for five hours. The reaction mixture was concentrated under reduced pressure, and added with cold water. The mixture was extracted with ether. The organic layer was washed with a saturated sodium chloride aqueous solution, and then dried with sodium sulfate. After filtration, the solvent was distilled under reduced pressure, and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:20)] to obtain the title compound (4.52 g, 89%).

1. temperatureunder cooling with ice
2. temperatureheated
3. temperaturerefluxed for five hours
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. additionadded with cold water
6. extractionThe mixture was extracted with ether
7. washThe organic layer was washed with a saturated sodium chloride aqueous solution
8. dry with materialdried with sodium sulfate
9. filtrationAfter filtration
10. distillationthe solvent was distilled under reduced pressure
11. customthe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:20)]

ORD record

ord-8c3b198e5d25434a8e5923be3d44962c

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943748B2