Carbon Tetrachloride → 2-[2-({[4-(Trifluoromethyl)phenyl]sulfonyl}oxy)phenyl]cyclopropanecarboxylic acid

HRID 1795124Notes

Reaction equation

HRID 1795124 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]2[CH2:21][CH:20]2[CH2:22][OH:23])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)(Cl)(Cl)Cl.C(#N)C.I([O-])(=O)(=O)=[O:35].[Na+]>O.[Ru](Cl)(Cl)Cl.O>[F:25][C:2]([F:24])([F:1])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]2[CH2:21][CH:20]2[C:22]([OH:35])=[O:23])(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6342AcetonitrileHCID 221855162-[2-(Hydroxymethyl)cyclopropyl]phenyl 4-(trifluoromethyl)benzenesulfonateHCID 23667635Sodium periodate

Product 1

HCID 221856342-[2-({[4-(Trifluoromethyl)phenyl]sulfonyl}oxy)phenyl]cyclopropanecarboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-[2-(hydroxymethyl)cyclopropyl]phenyl 4-(trifluoromethyl)-benzenesulfonate (0.70 g, 1.9 mmol), carbon tetrachloride (2.5 mL), acetonitrile (2.5 mL), water (3.8 mL), sodium periodate (1.8 g, 8.4 mmol) and ruthenium choride hydrate (75 mg, 0.4 mmol) is stirred at room temperature overnight. The reaction is partitioned between ethyl acetate and dilute HCl. The organic layer is filtered through anhydrous sodium sulfate, evaporated and purified on silica gel in ethyl acetate-methylene chloride-acetic acid mixtures. The product, 2-[2-({[4-(trifluoromethyl)phenyl]sulfonyl}oxy)phenyl]cyclopropanecarboxylic acid, is obtained as a mixture of isomers. A yield of 95% is obtained.

Workup

  1. customThe reaction is partitioned between ethyl acetate and dilute HCl
  2. filtrationThe organic layer is filtered through anhydrous sodium sulfate
  3. customevaporated
  4. custompurified on silica gel in ethyl acetate-methylene chloride-acetic acid mixtures

Sources & evidence

ORD record
ord-7b7a4e4992db4792893a49633a7aa668
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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