Water → 3,4-dibutylthiophene

HRID 2374690Notes

Reaction equation

HRID 2374690 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH3:4].Br[C:8]1[C:12](Br)=[CH:11][S:10][CH:9]=1.O>C(OCC)C.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:8]1[C:12]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:11][S:10][CH:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 184523,4-DibromothiopheneHCID 178418682HCID 178418682, compound

Product 1

HCID 112985343,4-dibutylthiopheneYield 64%

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

Butylmagnesium bromide (140 mmol) was added dropwise at 0° C. to a mixture solution of 3,4-dibromothiophene (50 mmol) and [1,3-bis (diphenylphosphino)propane]dichloronickel(II) (0.3 mmol) in 100 mL of dry diethyl ether. The resulting mixture was heated and refluxed for 6 hours. The reaction mixture was combined with water, and extracted with diethyl ether. The extract solution was derived over magnesium sulfate, and the solvent was evaporated therefrom to obtain a crude product. The crude product was purified by silica gel column chromatography and by distillation to obtain the intended product (32 mmol) in a 64% yield.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperaturerefluxed for 6 hours
  3. extractionextracted with diethyl ether
  4. customthe solvent was evaporated
  5. customto obtain a crude product
  6. distillationThe crude product was purified by silica gel column chromatography and by distillation

Sources & evidence

ORD record
ord-de883761642c48e3a70ebd0cdb4fe557
Source dataset
uspto-grants-2008_12
Patent number
US07462726B2

Reaction notes

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