Phenol → Phenyl 2-(4-fluorophenyl)ethenesulfonate

HRID 501249Notes

Reaction equation

HRID 501249 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][S:10](Cl)(=[O:12])=[O:11])=[CH:4][CH:3]=1.[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][S:10]([O:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 8471TriethylamineHCID 854347302-(4-Fluorophenyl)ethenesulfonyl chloride

Product 1

HCID 86243865Phenyl 2-(4-fluorophenyl)ethenesulfonateYield 70.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

163 g of 2-(4-fluorophenyl)ethenesulfonyl chloride were dissolved in 1.5 l of toluene and, at RT, 69.64 g of phenol were added. Subsequently, at RT, 103 ml of triethylamine were added dropwise, during which the temperature rose to 44° C. The mixture was then stirred at RT for 90 minutes, left to stand for 16 hours and stirred at RT for a further 2 hours. The solvent was then removed in vacuo, and the crude product was taken up in 2.5 l of EA. Washing 3 times with 750 ml of a saturated aqueous NaHCO3 solution was followed by washing 3 times with 750 ml of 2 N aqueous HCl solution each time. After drying over Na2SO4, the solvent was removed in vacuo. The product was then stirred in 350 ml of HEP for 1 hour and, on cooling, the product crystallized and was washed with HEP and dried under medium vacuum. 145.0 g of white crystals were obtained, mp 108° C.

Workup

  1. customrose to 44° C
  2. waitleft
  3. waitto stand for 16 hours
  4. stirringstirred at RT for a further 2 hours
  5. customThe solvent was then removed in vacuo
  6. washWashing 3 times with 750 ml of a saturated aqueous NaHCO3 solution
  7. washby washing 3 times with 750 ml of 2 N aqueous HCl solution each time
  8. dry with materialAfter drying over Na2SO4
  9. customthe solvent was removed in vacuo
  10. stirringThe product was then stirred in 350 ml of HEP for 1 hour
  11. temperatureon cooling
  12. customthe product crystallized
  13. washwas washed with HEP
  14. customdried under medium vacuum

Sources & evidence

ORD record
ord-4c91090d6897404d9c4c6238952e34c5
Source dataset
uspto-grants-2010_08
Patent number
US07772262B2

Reaction notes

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