Thiophenol → Ethyl Fluoro(phenylthio)acetate

HRID 986482Notes

Reaction equation

HRID 986482 reaction equation
CC[O-].[Na+].[C:5]1([SH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[F:12][CH:13](Br)[C:14]([O:16][CH2:17][CH3:18])=[O:15]>O1CCCC1>[F:12][CH:13]([S:11][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 2723922Sodium ethoxideHCID 2733407Acetic acid, 2-bromo-2-fluoro-, ethyl ester

Product 1

HCID 11148583Ethyl Fluoro(phenylthio)acetateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 150 ml of tetrahydrofuran (THF) were added 6.5 g (0.1 mole) of pulverized EtONa and 11.1 g (0.1 mole) of thiophenol and the mixture was refluxed for 10 minutes. Thereto was added 18.5 g (0.1 mole) of ethyl fluorobromoacetate and the mixture was refluxed for one hour with stirring. THF was removed by an evaporator and the precipitated NaBr was filtered. The organic layer was washed with water, dried and distilled to obtain 19.2 g (90%) of ethyl fluoro(phenylthio)acetate.

Workup

  1. temperaturethe mixture was refluxed for 10 minutes
  2. temperaturethe mixture was refluxed for one hour
  3. customTHF was removed by an evaporator
  4. filtrationthe precipitated NaBr was filtered
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationdistilled

Sources & evidence

ORD record
ord-034b39cd848445a797046d51f9e66e48
Source dataset
uspto-grants-1987_12
Patent number
US04713469

Reaction notes

Loading…