Toluene → 1-Methoxy-4-(pentafluoroethyl)benzene

HRID 1817840Notes

Reaction equation

HRID 1817840 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([F:8])([F:7])[C:4]([O-])=O.[K+].CN([CH:15]=[O:16])C.[C:17]1(C)[CH:22]=[CH:21]C=[CH:19][CH:18]=1>[Cu]I>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:4]([C:3]([F:8])([F:7])[C:2]([F:10])([F:9])[F:1])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6228DimethylformamideHCID 23667659Propanoic acid, 2,2,3,3,3-pentafluoro-, potassium salt (1:1)

Product 1

HCID 128719661-Methoxy-4-(pentafluoroethyl)benzene

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
140 °C

Procedure

8.3 g of potassium pentafluoropropionate and 9.8 g of CuI are introduced, under an inert atmosphere, into a 500 mL three-necked flasked equipped with Dean-Stark apparatus and a condenser. 90 mL of DMF and 110 mL of toluene are added. The medium is heated to 140° C. under nitrogen, and 80 mL of toluene are distilled off. The medium is then cooled to RT and then deoxygenated by sparging with nitrogen. 6 g of iodoanisole are then added and the mixture is then heated at 155° C. for 20 hours. After cooling to RT, the medium is diluted with 200 mL of a water/ethyl ether mixture. The medium is then filtered through Celite®. The organic phase is washed 3 times with water, dried over MgSO4 and then evaporated to give 4.3 g of a brown oil.

Workup

  1. customthree-necked flasked equipped with Dean-Stark apparatus and a condenser
  2. distillation80 mL of toluene are distilled off
  3. temperatureThe medium is then cooled to RT
  4. customdeoxygenated
  5. customby sparging with nitrogen
  6. addition6 g of iodoanisole are then added
  7. temperaturethe mixture is then heated at 155° C. for 20 hours
  8. temperatureAfter cooling to RT
  9. additionthe medium is diluted with 200 mL of a water/ethyl ether mixture
  10. filtrationThe medium is then filtered through Celite®
  11. washThe organic phase is washed 3 times with water
  12. dry with materialdried over MgSO4
  13. customevaporated

Sources & evidence

ORD record
ord-e4e89bb11fb54884ac95ad8e69af09c5
Source dataset
uspto-grants-2009_10
Patent number
US07598392B2

Reaction notes

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