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2,4-Dinitroiodobenzene → Diethyl 5-(3,5-dinitrophenyl)-2-furanphosphonate

HRID 895989
Notes
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Reaction equation

HRID 895989 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[O:10][C:9]([P:11]([O:16][CH2:17][CH3:18])(=[O:15])[O:12][CH2:13][CH3:14])=[CH:8][CH:7]=1)CCC.I[C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][C:29]=1[N+:37]([O-:39])=[O:38]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:34]([C:31]1[CH:32]=[C:33]([C:6]2[O:10][C:9]([P:11]([O:12][CH2:13][CH3:14])(=[O:15])[O:16][CH2:17][CH3:18])=[CH:8][CH:7]=2)[CH:28]=[C:29]([N+:37]([O-:39])=[O:38])[CH:30]=1)([O-:36])=[O:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 697302,4-DinitroiodobenzeneHCID 22280515Diethyl 5-tributylstannyl-2-furanphosphonate

Product 1

HCID 22349210Diethyl 5-(3,5-dinitrophenyl)-2-furanphosphonate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-Dioxane
Solvent

Conditions

Temperature
80 °C

Procedure

A mixture of diethyl 5-tributylstannyl-2-furanphosphonate (1 mmol), 1-iodo-2,4-dinitrobenzene (1 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.05 mmol) in 6 mL of dioxane was heated at 80° C. for 16 h. Evaporation of solvent and chromatography provided diethyl 5-(3,5-dinitrophenyl)-2-furanphosphonate as solid foam.

Workup

  1. customEvaporation of solvent and chromatography

Sources & evidence

ORD record
ord-6a9942365e4a4d52898f4e92ffd2f063
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06919322B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes