Cesium carbonate → HCID 21252717, Verbindung

HRID 1895711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1895711
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br/[CH:19]=[CH:20]/[C:21]([F:24])([F:23])[F:22].C(=O)([O-])[O-].[Cs+].[Cs+]>O.CN(C=O)C.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:19]=[CH:20]/[C:21]([F:24])([F:23])[F:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 27343144-Benzyloxy-phenylboronic acidHCID 57083831-Bromo-3,3,3-trifluoroprop-1-ene

Produkt 1

HCID 21252717HCID 21252717, VerbindungAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 4-(benzyloxy)phenylboronic acid (1026 mg, 4.50 mmol, Alfa Aesar), (E)-1-bromo-3,3,3-trifluoroprop-1-ene (262 mg, 1.5 mmol, SynQuest), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (122 mg, 0.15, Combiphos Catalysts, Inc.) and cesium carbonate (2444 mg, 7.50 mmol, Aldrich) in Water (0.5 mL) and DMF (3.0 mL) was heated under microwave conditions (90° C., 20 min). The reaction mixture was diluted with EtOAc and filtered. The filtrate was washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The residual was purified by flash chromatography on silica gel (0 to 100% EtOAc/hexanes) to yield the title compound (310 mg, 74%) as a pale yellow solid.

Aufarbeitung

  1. filtrationfiltered
  2. washThe filtrate was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residual was purified by flash chromatography on silica gel (0 to 100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f39619d0b8fa4293ac7f38ff6864c40a
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513424B2

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