Bis(4-tert-butylphenyl)iodanium hydrogen sulfate → Bis(4-tert-butylphenyl)iodonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate

HRID 2061315Notes

Reaction equation

HRID 2061315 reaction equation
S([O-])(O)(=O)=O.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([I+:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].[F:27][C:28]([F:41])([F:40])[C:29]([OH:39])([C:35]([F:38])([F:37])[F:36])[CH2:30][S:31]([O-:34])(=[O:33])=[O:32].[Na+]>C(Cl)Cl>[F:38][C:35]([F:36])([F:37])[C:29]([OH:39])([C:28]([F:41])([F:27])[F:40])[CH2:30][S:31]([O-:34])(=[O:33])=[O:32].[C:23]([C:20]1[CH:21]=[CH:22][C:17]([I+:16][C:13]2[CH:12]=[CH:11][C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:15][CH:14]=2)=[CH:18][CH:19]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 20205689Bis(4-tert-butylphenyl)iodanium hydrogen sulfateHCID 59445712Sodium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate

Product 1

HCID 86644258Bis(4-tert-butylphenyl)iodonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonateYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bis(4-tert-butylphenyl)iodonium hydrogen sulfate (0.02 mole equivalent) prepared in Synthesis Example 1-6, 0.024 mole equivalent of the aqueous solution of sodium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate prepared in Synthesis Example 1-9, and 70 g of methylene chloride were mixed and agitated at room temperature for 1 hour. After the agitation, the organic layer was separated, washed by water, and then concentrated under reduced pressure. The residue was recrystallized by adding diisopropyl ether, and then the obtained crystals were recovered and dried to obtain the intended bis(4-tert-butylphenyl)iodonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate (9.4 g of white crystals (yield 72%)). The structure of the intended product is shown below.

Workup

  1. additionwere mixed
  2. customAfter the agitation, the organic layer was separated
  3. washwashed by water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized
  6. additionby adding diisopropyl ether
  7. customthe obtained crystals were recovered
  8. customdried

Sources & evidence

ORD record
ord-22c4a858fb624b2ea64e2af2aa81e8bb
Source dataset
uspto-grants-2012_10
Patent number
US08283104B2

Reaction notes

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