Diphenyl Ether → 240482-96-6

HRID 2212623Notes

Reaction equation

HRID 2212623 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]1([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[F:41][C:42]([F:48])([F:47])[S:43]([OH:46])(=[O:45])=[O:44]>ClCCl>[F:41][C:42]([F:48])([F:47])[S:43]([O-:46])(=[O:45])=[O:44].[C:9]1([S+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:25]2[CH:24]=[CH:23][C:22]([O:21][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:27][CH:26]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 7583Diphenyl EtherHCID 9845Trifluoroacetic anhydrideHCID 13679Diphenyl sulfoxideHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 16213833240482-96-6Yield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 100 ml of dichloromethane were dissolved 10.1 g (0.05 mol) of diphenylsulfoxide and 8.51 g (0.05 mol) of diphenyl ether, and 12.6 g (0.06 mol) of trifluoroacetic anhydride was added thereto at 0° C. Then 7.5 g (0.05 mol) of trifluoromethanesulfonic acid was added dropwise thereto at 0 to 5° C., followed by gradually warming to room temperature and reacting for 2 hours with stirring. After completion of the reaction, the reaction solution was washed with 100 ml of water five times and concentrated under reduced pressure, followed by purifying the resulting crude product by a column chromatography to obtain 9.59 g (Yield: 38%) of diphenyl-4-phenoxyphenylsulfonium trifluoromethanesulfonate as a yellow oily substance.

Workup

  1. additionwas added
  2. customat 0° C
  3. customat 0 to 5° C.
  4. customAfter completion of the reaction
  5. washthe reaction solution was washed with 100 ml of water five times
  6. concentrationconcentrated under reduced pressure
  7. customby purifying the resulting crude product by a column chromatography

Sources & evidence

ORD record
ord-a06f3be8d44d47b38d7c49812f147533
Source dataset
uspto-grants-2006_09
Patent number
US07101918B2

Reaction notes

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