Diethyl Ether → HCID 86587149, compound

HRID 432537Notes

Reaction equation

HRID 432537 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCOCC.[F:14][C:15]1[C:20]([S:21]([C:23]2[C:28]([F:29])=[C:27]([F:30])[C:26]([F:31])=[C:25]([F:32])[C:24]=2[F:33])=O)=[C:19]([F:34])[C:18]([F:35])=[C:17]([F:36])[C:16]=1[F:37].[OH:38][S:39]([C:42]([F:45])([F:44])[F:43])(=[O:41])=[O:40]>C1C=CC=CC=1>[O-:41][S:39]([C:42]([F:45])([F:44])[F:43])(=[O:40])=[O:38].[F:14][C:15]1[C:20]([S+:21]([C:23]2[C:28]([F:29])=[C:27]([F:30])[C:26]([F:31])=[C:25]([F:32])[C:24]=2[F:33])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:19]([F:34])[C:18]([F:35])=[C:17]([F:36])[C:16]=1[F:37]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 62406Trifluoromethanesulfonic acidHCID 576190HCID 576190, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 86587149HCID 86587149, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 3M solution of phenylmagnesium bromide in ether (17 ml, 0.05 mole) is heated slowly to 80° C. under vacuum to remove the ether. 8 ml benzene and 17 ml heptane were then added and subsequently pentafluorophenyl sulfoxide (3.8 g, 0.01 mole), dissolved in 15 ml benzene, was added dropwise at 80° C. over one hour. After stirring for three hours, the solution is allowed to cool to room temperature, followed by the addition of 33 ml of 25% triflic acid. The organic layer was separated and extracted twice with 10 ml of 5% triflic acid. The aqueous layers were combined and extracted three times with 100 ml diclhoromethane and solvent removed after drying over magnesium sulfate, yielding 600 mg (10%) of di(pentafluorophenyl)phenyl sulfonium triflate. The structure was confirmed by 1H/13C NMR.

Workup

  1. customto remove the ether
  2. addition8 ml benzene and 17 ml heptane were then added
  3. additionwas added dropwise at 80° C. over one hour
  4. customThe organic layer was separated
  5. extractionextracted twice with 10 ml of 5% triflic acid
  6. extractionextracted three times with 100 ml diclhoromethane and solvent
  7. customremoved
  8. dry with materialafter drying over magnesium sulfate

Sources & evidence

ORD record
ord-bacc2b8ac87c4fd88dfd9618f742db46
Source dataset
uspto-grants-2003_12
Patent number
US06664022B1

Reaction notes

Loading…