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

HRID 2236426Notes

Reaction equation

HRID 2236426 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-fe0d95519f4a4c3fa213313ff6d8e065
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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