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2-(Tributylstannyl)furan → 2-Furan-2-yl-5-hydroxy-benzonitrile

HRID 2236473
Notes
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Reaction equation

HRID 2236473 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:9]=1)[C:7]#[N:8].[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[Sn](CCCC)(CCCC)CCCC>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:9][C:6]=1[C:7]#[N:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 686960525-Hydroxy-2-iodobenzonitrile

Product 1

HCID 686948832-Furan-2-yl-5-hydroxy-benzonitrile

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Hydroxy-2-iodo-benzonitrile (200 mg, 0.82 mmol) and PdCl2(PPh3)2 (20 mg, 0.028 mmol) and 2-furyltributyltin (400 g, 1.12 mmol) in N,N-dimethylformamide (5 mL) is degassed and heated at 100° C. for 15 min. After the mixture cooled to room temperature, an aqueous work up is performed and the product is isolated from chromatography (100 mg, 66%). MS (ESI): 184 (M−1)−1.

Workup

  1. temperatureAfter the mixture cooled to room temperature
  2. customthe product is isolated from chromatography (100 mg, 66%)

Sources & evidence

ORD record
ord-71a6bb55f69e48bf953a05f7e80e4ce8
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07713994B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes