Chloroform → 2-Furan-3-yl-5-hydroxy-benzonitrile

HRID 2236426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2236426
[OH:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:9]=1)[C:7]#[N:8].C(Cl)(Cl)Cl.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[O:28]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29]1.[F-].[Cs+]>CN(C)C=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:28]1[CH:32]=[CH:31][C:30]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:9][C:6]=2[C:7]#[N:8])=[CH:29]1

Komponenten

8

Edukt 5

HCID 6212ChloroformHCID 25953Cesium fluorideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2734358Furan-3-boronic acidHCID 686960525-Hydroxy-2-iodobenzonitrile

Produkt 1

HCID 593001112-Furan-3-yl-5-hydroxy-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Hydroxy-2-iodo-benzonitrile (70 mg, 0.29 mmol), Pd2(dba)3.CHCl3(25 mg, 0.01 mmol) and P(tBu)3 (0.05 mL, 10% in hexane, 0.016 mmol), 3-furanboronic acid (40 mg, 0.36 mmol) and CsF (200 mg, 1.32 mmol) were suspended in N,N-dimethylformamide (5 mL). The mixture is then degassed and stirred at room temperature for 4 hours. After aqueous workup, the residue is purified with chromatography and directly employed in the next step.

Aufarbeitung

  1. customThe mixture is then degassed
  2. customAfter aqueous workup, the residue is purified with chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fe0d95519f4a4c3fa213313ff6d8e065
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713994B2

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