Water → Methyl 4'-Cyano[1,1'-biphenyl]-2-carboxylate

HRID 10070

Reaktionsgleichung

Reaktionsgleichung von HRID 10070
O.C(=O)([O-])[O-].[K+].[K+].I[C:9]1[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].[C:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)#[N:20]>[Pd](Cl)Cl.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C1COCC1>[C:19]([C:21]1[CH:26]=[CH:25][C:24]([C:9]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:23][CH:22]=1)#[N:20]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 69132Benzoic acid, 2-iodo-, methyl esterHCID 27343264-Cyanophenylboronic acid

Produkt 1

HCID 21988942Methyl 4'-Cyano[1,1'-biphenyl]-2-carboxylateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10876480Bis(tri-o-tolylphosphine)palladium(II) DichlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 500 mL of THF was added water (18.4 mL, 1.02 mol), potassium carbonate (70.5 g, 0.510 mol), methyl 2-iodobenzoate (53.5 g, 0.204 mol), 4-cyano-phenylboronic acid (30.0 g, 0.204 mol) and bis-(tri-o-tolylphosphine) palladium (II) chloride (1.65 g, 2.04 mmol). This mixture was heated to reflux for 3.5 hours and then cooled to ambient temperature for continued stirring overnight. The solvent was then removed under reduced pressure prior to dilution with EtOAc/water. The organic layer was extracted with additional EtOAc. The combined organics were washed with water, then brine. The organics were then dried over sodium sulfate, filtered, and then concentrated to obtain the crude product. This crude product was passed through a silica pad, eluting with 8:1 heptane:EtOAc to get 41.6 grams of methyl 4′-cyano-1,1′-biphenyl-2-carboxylate.

Aufarbeitung

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 3.5 hours
  3. customThe solvent was then removed under reduced pressure
  4. extractionThe organic layer was extracted with additional EtOAc
  5. washThe combined organics were washed with water
  6. dry with materialThe organics were then dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto obtain the crude product
  10. washeluting with 8:1 heptane

Quellen und Nachweise

ORD-Eintrag
ord-5ae0c0d393cb48bfbc9062688fae2658
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091380B2

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