Water → HCID 21200004, compound

HRID 2374691Notes

Reaction equation

HRID 2374691 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Br[C:14]1[C:18](Br)=[CH:17][S:16][CH:15]=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:14]1[C:18]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:17][S:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 962WaterHCID 184523,4-DibromothiopheneHCID 178418384HCID 178418384, compound

Product 1

HCID 21200004HCID 21200004, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

Decylmagnesium 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 dried 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 (38 mmol) in a 76% yield.

Workup

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

Sources & evidence

ORD record
ord-104f6862d2e64c059c779a78e84b612d
Source dataset
uspto-grants-2008_12
Patent number
US07462726B2

Reaction notes

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