Vinyl Acetate → 1-Fluoro-2-(2-vinyloxyethyl)-benzene

HRID 20330

Reaktionsgleichung

Reaktionsgleichung von HRID 20330
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10].[C:11](OC=C)(=O)[CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir].C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][O:10][CH:11]=[CH2:12]

Komponenten

6

Edukt 3

HCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 27332962-(2-Fluorophenyl)ethan-1-ol

Produkt 1

HCID 685635321-Fluoro-2-(2-vinyloxyethyl)-benzeneAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6436381Chloro(1,5-cyclooctadiene)iridium(I) dimerKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Combine 2-(2-fluorophenyl)-ethanol (3.08 g, 22.0 mmol), vinyl acetate (4 mL, 43.3 mmol), anhydrous toluene (22 mL), chloro(1,5-cyclooctadiene)iridium(I) dimer (155 mg, 0.231 mmol), and anhydrous sodium carbonate (1.5 g, 14.2 mmol) in a dry round-bottom flask fitted with a reflux condensor under a nitrogen atmosphere. Heat the resulting mixture to 95° C. for 5 hours. Cool the reaction mixture to room temperature. Vacuum filter the resultant slurry to remove inorganic precipitates, washing the collected solid with hexanes. Concentrate and purify (silica gel chromatography, eluting with hexanes) to give the title compound as a yellow oil (2.64 g, 72%).

Aufarbeitung

  1. temperatureCool the reaction mixture to room temperature
  2. filtrationVacuum filter the resultant slurry
  3. customto remove inorganic precipitates
  4. washwashing the collected solid with hexanes
  5. concentrationConcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7b1b0cb0cdd642c8a96a6098f2f2bb17
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745438B2

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