Hexane → HCID 87183733, compound

HRID 551334Notes

Reaction equation

HRID 551334 reaction equation
[Br-].[F:2][C:3]([F:8])([F:7])[C:4]([Zn+])=[CH2:5].[Cl:9][C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][C:11]=1[C:17]([F:20])([F:19])[F:18].CCCCCC>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:4]([C:3]([F:8])([F:7])[F:2])=[CH2:5])=[CH:12][C:11]=1[C:17]([F:20])([F:19])[F:18]

Participants

6

Reactant 3

HCID 8058HexaneHCID 431453921-Chloro-4-iodo-2-(trifluoromethyl)benzeneHCID 178477747HCID 178477747, compound

Product 1

HCID 87183733HCID 87183733, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 1M solution of 1-(trifluoromethyl)ethenyl zinc bromide in tetrahydrofuran (see J. Org. Chem. 1991, 56, 7336 for preparation) (53 mL) under nitrogen atmosphere was added 2-chloro-5-iodobenzotrifluoride (7.1 g), followed by the addition of dichlorobis(triphenylphosphine)palladium(II) (0.65 g). The mixture was stirred under reflux for 2.5 hours and then cooled to room temperature. To the resulting mixture was added hexane (100 mL) and filtered, and the filtrate was washed with water (50 mL) and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide a residue. The residue was purified by column chromatography on silica gel eluted with hexane to afford the title compound as colorless oil (4.8 g).

Workup

  1. temperatureunder reflux for 2.5 hours
  2. filtrationfiltered
  3. washthe filtrate was washed with water (50 mL) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a residue
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluted with hexane

Sources & evidence

ORD record
ord-3ee0830583c148b9b67144e57051eb12
Source dataset
uspto-grants-2011_05
Patent number
US07947715B2

Reaction notes

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