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

HRID 16321

反応式

HRID 16321 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
80 °C

実験手順

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:

後処理

  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)

出典と根拠

ORDレコード
ord-563ba4ee05cd43ccbe1fbf9ec4b76996
出典データセット
uspto-grants-2010_06
特許番号
US07737141B2

関連ノート

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