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Potassium Phosphate, Tribasic → HCID 68507568, Verbindung

HRID 1715152
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1715152
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](I)=[C:7]([O:12][CH2:13][CH3:14])[CH:6]=1)[CH3:2].[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][C:8]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)=[C:7]([O:12][CH2:13][CH3:14])[CH:6]=1)=[O:15])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 23090718Ethyl 3-ethoxy-4-iodobenzoate

Produkt 1

HCID 68507568HCID 68507568, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3-ethoxy-4-iodo-benzoic acid ethyl ester (0.76 g, 2.37 mmol, 1.0 equiv; [CAS RN 741699-04-7]) in anhydrous DMF (12 mL) under Ar was added 4-fluorophenyl boronic acid (0.40 g, 2.86 mmol, 1.20 equiv), K3PO4 (0.86 g, 4.04 mmol, 1.70 equiv) and tetrakis(triphenylphosphine) palladium(0) (0.082 g, 0.071 mmol, 0.03 equiv) and the reaction mixture heated to 80° C. After 16 h, the reaction mixture was poured on crashed ice/NH4Cl, extracted twice with ethyl acetate, the combined organic phases washed with water and a sat. solution of NaCl, dried over MgSO4 and concentrated by evaporation under reduced pressure. The crude material was purified with silica column chromatography eluting with hexane/ethyl acetate (95:5) to yield 0.51 g (75%) of the title compound as a colorless oil. MS (ISP): 289.3 [M+H]+.

Aufarbeitung

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with ethyl acetate
  3. washthe combined organic phases washed with water
  4. dry with materiala sat. solution of NaCl, dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe crude material was purified with silica column chromatography
  7. washeluting with hexane/ethyl acetate (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-4ef4acdfdd1d4818ab564ea496c9ba97
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07799806B2

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