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

HRID 16353

Reaction equation

HRID 16353 reaction equation
[F-].[Cs+].O1CCOCC1.Br[C:10]1[CH:15]=[C:14]([F:16])[C:13]([F:17])=[C:12]([F:18])[CH:11]=1.[CH:19](/B(O)O)=[CH:20]\[CH3:21]>O.CCCCCC>[F:16][C:14]1[CH:15]=[C:10](/[CH:19]=[CH:20]/[CH3:21])[CH:11]=[C:12]([F:18])[C:13]=1[F:17]

Participants

7

Reactant 4

HCID 25953Cesium fluorideHCID 312751,4-DioxaneHCID 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 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

In nitrogen atmosphere, tetrakistriphenylphosphine palladium(0) (4.66 g) and cesium fluoride (21.4 g) were added to a solution mixture of dioxane (95 mL) and water (5 mL) of 1-bromo-3,4,5-trifluorobenzene (8.5 g) and trans-1-propen-1-ylboronic acid (4.1 g). The resulting reaction solution was stirred at 80° C. for 5 hr and then cooled to room temperature, and hexane and water were added thereto. The insoluble matter was removed by filtration. The organic layer of the filtrate was separated and washed with water. The insoluble matter was removed by filtration again. The filtrate was washed with water and then with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane) to give 5.83 g of the title compound. The physical property values of this compound were as follows:

Workup

  1. customThe resulting reaction solution
  2. temperaturecooled to room temperature
  3. customThe insoluble matter was removed by filtration
  4. customThe organic layer of the filtrate was separated
  5. washwashed with water
  6. customThe insoluble matter was removed by filtration again
  7. washThe filtrate was washed with water
  8. dry with materialwith saturated saline, dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-930aae2dda3b4ecab88de5f4c21b575b
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Linked notes

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