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Ethanol → 3-Fluoro-4-methoxymethoxy-5-vinylbenzoic acid methyl ester

HRID 423245
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 423245
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([O:11][CH2:12][O:13][CH3:14])=[C:6](Br)[CH:5]=1.[CH2:17](OB(C=C)OCCCC)[CH2:18]CC.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:5]=[C:6]([CH:17]=[CH2:18])[C:7]([O:11][CH2:12][O:13][CH3:14])=[C:8]([F:10])[CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 236543Dibutyl Vinylboronate (stabilized with Phenothiazine)HCID 586297383-Bromo-5-fluoro-4-methoxymethoxybenzoic acid methyl ester

Produkt 1

HCID 586297733-Fluoro-4-methoxymethoxy-5-vinylbenzoic acid methyl esterAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 3-bromo-5-fluoro-4-methoxymethoxybenzoic acid methyl ester (300 mg) and vinylboronic acid dibutyl ester (226 mg) in toluene (4 mL)-ethanol (2 mL) were added dichlorobis(triphenylphosphine)palladium (II) (36 mg) and an aqueous solution (1 mL) of sodium carbonate (217 mg). The mixture was stirred at 100° C. for 8 hours, and then allowed to stand for cooling down to room temperature. The resulting insoluble materials were filtered through a Celite pad, and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. After concentration in vacuo, the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=30:1, v/v) to give the title compound (190 mg).

Aufarbeitung

  1. temperaturefor cooling down to room temperature
  2. filtrationThe resulting insoluble materials were filtered through a Celite pad
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationAfter concentration in vacuo
  8. customthe residue was purified by column chromatography on silica gel (hexane

Quellen und Nachweise

ORD-Eintrag
ord-35b09a2d5ceb4649ab4ad837e417dca1
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08101774B2

Notizen zur Reaktion

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