Chloroform → HCID 87588252, compound

HRID 1818644Notes

Reaction equation

HRID 1818644 reaction equation
[Cl-].[CH2:2]([O:10][C:11]1[CH:16]=[CH:15][C:14]([I+:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[F:24][C:25]([F:40])([S:36]([O-:39])(=[O:38])=[O:37])[C:26]([F:35])([F:34])[C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29].[K+].C(Cl)(Cl)Cl>O.C1COCC1>[F:40][C:25]([F:24])([S:36]([O-:39])(=[O:38])=[O:37])[C:26]([F:34])([F:35])[C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29].[CH2:2]([O:10][C:11]1[CH:12]=[CH:13][C:14]([I+:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 23675274Potassium perfluorobutanesulfonateHCID 71353995[4-(Octyloxy)phenyl](phenyl)iodanium chloride

Product 1

HCID 87588252HCID 87588252, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

4-octyloxyphenylphenyl iodonium chloride (15.34 g) was dissolved in water and THF in a beaker and a solution of potassium perfluorobutane sulfonate (11.67 g) in water and THF solution was added on stirring. After six hours, chloroform (200 ml) was added and stirred for 3 hours. The chloroform layer was washed several times with water, dried over anhydrous sodium sulfate, filtered, evaporated to oil which was added to hexane (500 ml), and a precipitate formed. The precipitate was filtered and re-dissolved in dichloromethane and precipitated in hexane, filtered, dried in the vacuum oven, yielding 22.0 g of product.

Workup

  1. stirringstirred for 3 hours
  2. washThe chloroform layer was washed several times with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated to oil which
  6. additionwas added to hexane (500 ml)
  7. customa precipitate formed
  8. filtrationThe precipitate was filtered
  9. dissolutionre-dissolved in dichloromethane
  10. customprecipitated in hexane
  11. filtrationfiltered
  12. customdried in the vacuum oven

Sources & evidence

ORD record
ord-6fcc1b80750142e4999bba2d2fa7c592
Source dataset
uspto-grants-2009_10
Patent number
US07601480B2

Reaction notes

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