Tetrahydrofuran → HCID 87183733, compound

HRID 1880254Notes

Reaction equation

HRID 1880254 reaction equation
O1CCCC1.[Br-].[F:7][C:8]([F:13])([F:12])[C:9]([Zn+])=[CH2:10].[Cl:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][C:16]=1[C:22]([F:25])([F:24])[F:23]>CCCCCC>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:9]([C:8]([F:13])([F:12])[F:7])=[CH2:10])=[CH:17][C:16]=1[C:22]([F:25])([F:24])[F:23]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 431453921-Chloro-4-iodo-2-(trifluoromethyl)benzeneHCID 178477747HCID 178477747, compound

Product 1

HCID 87183733HCID 87183733, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a nitrogen atmosphere, to 53 mL of a 1M tetrahydrofuran solution of 1-trifluoromethylethenyl zinc bromide prepared according to a method described in the literatures, 7.1 g of 2-chloro-5-iodobenzotrifluoride and 0.65 g of dichlorobis(triphenylphosphine) palladium (II) were added and the resultant mixture was stirred while heating the mixture to reflux for 2.5 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and 200 mL of hexane was added to the reaction mixture, followed by filtering off the deposited insoluble substance. The resultant filtrate was washed with water (50 mL×1) and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with hexane to obtain 4.8 g of the objective substance as a colorless oily substance.

Workup

  1. additionwere added
  2. temperaturewhile heating the mixture
  3. temperatureto reflux for 2.5 hours
  4. customAfter the completion of the reaction
  5. waitthe reaction mixture was left
  6. filtrationby filtering off the deposited insoluble substance
  7. washThe resultant filtrate was washed with water (50 mL×1)
  8. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe resultant residue was purified by silica gel column chromatography
  11. washeluting with hexane
  12. customto obtain 4.8 g of the objective substance as a colorless oily substance

Sources & evidence

ORD record
ord-5f5da57bb87d40c09c79aba1efcccd91
Source dataset
uspto-grants-2012_11
Patent number
US08318757B2

Reaction notes

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