Dimethyl Sulfoxide → HCID 53653030, compound

HRID 2395805Notes

Reaction equation

HRID 2395805 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:17])=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CS(C)=O.Br[C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[Br:25]>C1(C)C=CC=CC=1>[Br:25][C:24]([F:27])([F:26])[C:23]([F:29])([F:28])[O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:17])=[CH:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[Br:25])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethaneHCID 6566934,4'-Dihydroxy-alpha-methylstilbene

Product 1

HCID 53653030HCID 53653030, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
24 °C

Procedure

4,4'-bis(hydroxy)-α-methylstilbene (100.0 g, 0.442 mole) is added to a 3 liter, 4 necked round bottomed flask along with DMSO (dimethylsulfoxide) (1150 ml) and toluene (350 ml). The resulting mixture is deoxygenated with nitrogen for 15 minutes, then KOH (58.4 g, 0.884 mole as 85 percent pellets, the remaining 15 percent being water) is added all at once. The mixture is stirred and heated to reflux, and water is removed azeotropically by distillation of the water/toluene azeotrope for a total of 10 hours. A Soxhlet extractor containing a drying bed of anhydrous Na2SO4 is placed on the reactor, and the toluene is refluxed through this drying bed to remove residual water. Toluene (260 ml) is removed by simple distillation, then the remaining mixture is cooled to 24° C. 1,2-Dibromotetrafluoroethane (276 g, 1.06 mole) is added slowly over 30 minutes, and the reaction mixture is stirred at 24° C. for 8 hours. After filtration and evaporation, the residue is flushed through a column of alumina using hexane as the eluent. Hexane is removed by evaporation, and the resulting residue weighs 109.4 g (0.19 mole) for an isolated yield of 42 percent.

Workup

  1. customThe resulting mixture is deoxygenated with nitrogen for 15 minutes
  2. additionis added all at once
  3. temperatureheated
  4. temperatureto reflux
  5. customwater is removed azeotropically by distillation of the water/toluene
  6. customazeotrope for a total of 10 hours
  7. additionA Soxhlet extractor containing a drying bed of anhydrous Na2SO4
  8. temperaturethe toluene is refluxed through this drying bed
  9. customto remove residual water
  10. customToluene (260 ml) is removed by simple distillation
  11. stirringthe reaction mixture is stirred at 24° C. for 8 hours
  12. filtrationAfter filtration and evaporation
  13. customthe residue is flushed through a column of alumina
  14. customHexane is removed by evaporation

Sources & evidence

ORD record
ord-fac4a41d12264285bcb175f678222119
Source dataset
uspto-grants-1996_02
Patent number
US05489623

Reaction notes

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