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

HRID 16321

반응식

HRID 16321 반응식
[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]

참가 물질

7

반응물 4

HCID 25953Cesium fluorideHCID 312751,4-DioxaneHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 6157276((1E)-prop-1-en-1-yl)boronic acid

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8058Hexane용매

반응 조건

온도
80 °C

실험 절차

In nitrogen atmosphere, tetrakistriphenyl-phosphine 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), trans-1-propen-1-ylboronic acid (4.1 g). The resulting reaction solution was stirred at 80° C. for 5 hr and cooled to room temperature. To the reaction solution, hexane and water were added. The precipitated insoluble matter was removed by filtration, and the organic layer was separated. The obtained organic layer was washed with water, and the insoluble matter was removed by filtration again. The organic layer was separated. The obtained organic layer 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 (eluting solvent: hexane) to give 5.83 g of the title compound. The physical property values of this compound were as follows:

후처리

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

출처 및 근거

ORD 기록
ord-563ba4ee05cd43ccbe1fbf9ec4b76996
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737141B2

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