Water → 1-Methyl-4-(pentafluoroethyl)benzene

HRID 1873493Notes

Reaction equation

HRID 1873493 reaction equation
IC1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[F:9][C:10]([F:18])([C:14]([F:17])([F:16])[F:15])[C:11]([O-])=O.[K+].O.CCOCC>CN(C=O)C.[Cu](I)I>[CH3:8][C:5]1[CH:6]=[CH:7][C:11]([C:10]([F:18])([F:9])[C:14]([F:17])([F:16])[F:15])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 122074-IodotolueneHCID 23667659Propanoic acid, 2,2,3,3,3-pentafluoro-, potassium salt (1:1)

Product 1

HCID 141135221-Methyl-4-(pentafluoroethyl)benzeneYield 92.6%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Procedure adapted from Syn. Comm., (1988) 18(9):965-972. A mixture of copper iodide (129 g, 679 mmol), 1-iodo-4-methylbenzene (1) (74 g, 339 mmol) and potassium 2,2,3,3,3-pentafluoropropanoate (120 g, 594 mmol) were dissolved in DMF (500 mL) and heated to 120° C. for 30 minutes and then heated at 160° C. for 4 hours, after which the mixture was allowed to cool to room temperature. Water (200 mL) and ether (200 mL) were added and after stirring for 30 minutes the solids were filtered and washed with ether. The phases were separated and the organic layer was washed with brine/water (3×250 mL). The organic layer was dried and concentrated to yield 1-methyl-4-(perfluoroethyl)benzene (66 g, 92%) as a dark oil.

Workup

  1. temperatureheated at 160° C. for 4 hours
  2. temperatureto cool to room temperature
  3. filtrationwere filtered
  4. washwashed with ether
  5. customThe phases were separated
  6. washthe organic layer was washed with brine/water (3×250 mL)
  7. customThe organic layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1673ee0e1fff41bfb174b4401ed244df
Source dataset
uspto-grants-2012_11
Patent number
US08304407B2

Reaction notes

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