Triethylamine → bis(4-tert-butylphenyl)iodonium 2-(2,2-Dimethylpropionyloxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonate

HRID 2061316Notes

Reaction equation

HRID 2061316 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([OH:13])([C:9]([F:12])([F:11])[F:10])[CH2:4][S:5]([O-:8])(=[O:7])=[O:6].[C:16]([C:20]1[CH:25]=[CH:24][C:23]([I+:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C.[C:44](Cl)(=[O:49])[C:45]([CH3:48])([CH3:47])[CH3:46]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:46][C:45]([CH3:48])([CH3:47])[C:44]([O:13][C:3]([C:2]([F:1])([F:14])[F:15])([C:9]([F:12])([F:10])[F:11])[CH2:4][S:5]([O-:8])(=[O:7])=[O:6])=[O:49].[C:33]([C:30]1[CH:31]=[CH:32][C:27]([I+:26][C:23]2[CH:22]=[CH:21][C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:25][CH:24]=2)=[CH:28][CH:29]=1)([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 86644258Bis(4-tert-butylphenyl)iodonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate

Product 1

HCID 86644259bis(4-tert-butylphenyl)iodonium 2-(2,2-Dimethylpropionyloxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonateYield 24.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a mixture solution of 6.5 g (0.010 mole) of bis(4-tert-butylphenyl)iodonium 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropane-1-sulfonate prepared in Synthesis Example 1-13, 2.2 g (0.022 mole) of triethylamine, 0.2 g (0.002 mole) of 4-dimethylaminopyridine, and 25 g of methylene chloride was added 2.4 g (0.020 mole) of pivaloyl chloride, and they were stirred at room temperature for 8 hours. Thereafter, the reaction was terminated by adding 22 g of 5% hydrochloric acid, and then the organic layer was separated, washed by water, and concentrated under reduced pressure. Into the concentrated solution was added methyl isobutyl ketone, and the resulted mixture was concentrated again under reduced pressure to distil the remaining water out. The obtained residue was recrystallized by adding diisopropyl ether, and then the crystals were recovered and dried to obtain the intended bis(4-tert-butylphenyl)iodonium 2-(2,2-Dimethylpropionyloxy)-3,3,3-trifluoro-2-trifluoromethylpropane-1-sulfonate (1.8 g of white crystals (yield 23%)). The structure of the intended product is shown below.

Workup

  1. customThereafter, the reaction was terminated
  2. additionby adding 22 g of 5% hydrochloric acid
  3. customthe organic layer was separated
  4. washwashed by water
  5. concentrationconcentrated under reduced pressure
  6. additionInto the concentrated solution was added methyl isobutyl ketone
  7. concentrationthe resulted mixture was concentrated again under reduced pressure
  8. customto distil the remaining water out
  9. customThe obtained residue was recrystallized
  10. additionby adding diisopropyl ether
  11. customthe crystals were recovered
  12. customdried

Sources & evidence

ORD record
ord-b2b7bcb42a4643fdbdbfcc8589431497
Source dataset
uspto-grants-2012_10
Patent number
US08283104B2

Reaction notes

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