1-Bromododecane → 3-Dodecylthiophene

HRID 888670Notes

Reaction equation

HRID 888670 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Br[C:16]1[CH:20]=[CH:19][S:18][CH:17]=1>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:3]([C:16]1[CH:20]=[CH:19][S:18][CH:17]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 89191-BromododecaneHCID 133833-BromothiopheneHCID 5462224Magnesium

Product 1

HCID 27336553-DodecylthiopheneYield 85%

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

Dried ethyl ether (40 ml) was added to activated magnesium (1.22 g; 50 mmol), and 1-bromododecane (12.46 g; 50 mmol) was added thereto to prepare a Grignard reagent. Then, Ni(dppp)Cl2 (33 mg) was added thereto, and 3-bromothiophene (8 g; 49 mmol) dissolved in 10 ml of ether was slowly added dropwise. The reaction solution was refluxed for one day, and then a mixture of 2N HCl/ice (50 ml) was added to terminate the reaction. The resultant was extracted by using ethyl ether, and the solvent was distilled off under reduced pressure. The residue was dissolved in DMF (50 ml) and filtered to remove remaining paraffin. The filtrate was concentrated, and then the residue was distilled off under vacuum to obtain a colorless liquid of 3-dodecylthiophene (10.5 g; 85%).

Workup

  1. additionwas added
  2. additionwas slowly added dropwise
  3. temperatureThe reaction solution was refluxed for one day
  4. additionwas added
  5. customto terminate
  6. customthe reaction
  7. extractionThe resultant was extracted
  8. distillationthe solvent was distilled off under reduced pressure
  9. dissolutionThe residue was dissolved in DMF (50 ml)
  10. filtrationfiltered
  11. customto remove
  12. concentrationThe filtrate was concentrated
  13. distillationthe residue was distilled off under vacuum

Sources & evidence

ORD record
ord-07e923233ab444039188ad2166428110
Source dataset
uspto-grants-2012_08
Patent number
US08247803B2

Reaction notes

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