o-Iodonitrobenzene → 2-(2-nitrophenyl)thiophene

HRID 1987700Notes

Reaction equation

HRID 1987700 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)CCC.I[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27]>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>[N+:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)([O-:28])=[O:27]

Participants

5

Reactant 2

HCID 69115o-IodonitrobenzeneHCID 27793732-(Tri-n-butylstannyl)thiophene

Product 1

HCID 91672612-(2-nitrophenyl)thiopheneYield 80%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Bis(triphenylphosphine)palladium(II) chloride (350 mg) and 2-(tributylstannyl)thiophene (57 g, 0.15 mol) were added to a solution of 1-iodo-2-nitrobenzene (35 g, 0.14 mol) in 500 ml of N,N-dimethylformamide. This mixture was heated for 16 h to 100° C. After concentration in vacuo, the residue was taken up in diethyl ether, washed with water and brine, dried over magnesium sulfate and evaporated. The remaining oil was purified by silica gel chromatography using ethyl acetate and hexane as eluents, yielding 23 g of 2-(2-nitro-phenyl)-thiophene.

Workup

  1. temperatureThis mixture was heated for 16 h to 100° C
  2. concentrationAfter concentration in vacuo
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe remaining oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e71e761870a84f0b9ce3eb9688edd67e
Source dataset
uspto-grants-2009_06
Patent number
US07553798B2

Reaction notes

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