Methanol → 1-[(2-Bromoethyl)sulfanyl]-3-fluorobenzene

To 2 mL of a methanol solution containing 0.83 g of 28% sodium methoxide/methanol, 1.0 mL of 1,2-dibromoethane and 0.50 g of 3-fluorobenzenethiol were added under cooling with ice, the mixture was stirred at the same temperature for 1 hour, at room temperature for 2 hours, and at 50° C. for 1 hour, and then the reaction mixture was refluxed by heating for 5 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added thereto. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane] to obtain 0.62 g of a pale yellow oily substance, 1-(3-fluorophenyl)thio-2-bromoethane.

1. additionwere added
2. temperatureunder cooling with ice
3. waitat 50° C. for 1 hour
4. temperaturethe reaction mixture was refluxed
5. temperatureby heating for 5 hours
6. temperatureThe reaction mixture was cooled to room temperature
7. customThe organic layer was separated
8. washwashed with an aqueous saturated sodium chloride solution
9. dry with materialdried over anhydrous magnesium sulfate
10. customthe solvent was removed under reduced pressure
11. customThe residue thus obtained
12. customwas purified by silica gel column chromatography [eluent; hexane]

ORD record

ord-4c599ba040dc492a8ebc1ad9adb1f598

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524738B2