Hexane → 1,2,3-trifluoro-5-((E)-propenyl)benzene

HRID 1436105Notes

Reaction equation

HRID 1436105 reaction equation
[F-].[Cs+].Br[C:4]1[CH:9]=[C:8]([F:10])[C:7]([F:11])=[C:6]([F:12])[CH:5]=1.[CH:13](/B(O)O)=[CH:14]\[CH3:15].CCCCCC>O1CCOCC1.O>[F:10][C:8]1[CH:9]=[C:4](/[CH:13]=[CH:14]/[CH3:15])[CH:5]=[C:6]([F:12])[C:7]=1[F:11]

Participants

7

Reactant 4

HCID 8058HexaneHCID 25953Cesium fluorideHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 6157276((1E)-prop-1-en-1-yl)boronic acid

Product 1

HCID 687165151,2,3-trifluoro-5-((E)-propenyl)benzeneYield 84.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Tetrakistriphenylphosphine palladium (0) (4.66 g) and cesium fluoride (21.4 g) were added to a solution of 1-bromo-3,4,5-trifluorobenzene (8.5 g) and trans-1-propen-1-ylboronic acid (4.1 g) in dioxane (95 ml) and water (5 ml) in a nitrogen atmosphere, and the reaction solution was stirred at 80° C. for five hours. The reaction solution was returned to room temperature. Then, hexane and water were added to the reaction solution, and the insoluble matter was removed by filtration. The organic layer was separated and then washed with water, and the insoluble matter was removed by filtration again. The organic layer was separated and then sequentially washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane) to obtain 5.83 g of the title compound.

Workup

  1. customwas returned to room temperature
  2. customthe insoluble matter was removed by filtration
  3. customThe organic layer was separated
  4. washwashed with water
  5. customthe insoluble matter was removed by filtration again
  6. customThe organic layer was separated
  7. washsequentially washed with water and brine
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe resulting crude product was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-22356bfd4e4744c38fc19a635aea4604
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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