2-(Tri-n-butylstannyl)thiophene → HCID 21945618, compound

HRID 2216713Notes

Reaction equation

HRID 2216713 reaction equation
Br[C:2]1[S:3][C:4](Br)=[C:5]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C([Sn](CCCC)(CCCC)[C:29]1[S:30][CH:31]=[CH:32][CH:33]=1)CCC>O1CCCC1.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>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:2]1[S:3][C:4]([C:31]2[S:30][CH:29]=[CH:33][CH:32]=2)=[C:5]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 219456172,5-Dibromo-3,4-dioctylthiophene

Product 1

HCID 21945618HCID 21945618, compoundYield 145.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a dry box under an inert atmosphere, Pd(PPh3)2Cl2 (0.15 gram, 0.2 mmol) was added to a mixture of 2,5-dibromo-3,4-dioctylthiophene (4.2 grams, 9 mmol) and 2-(tributylstannyl)-thiophene (7.4 grams, 19.8 mmol) in anhydrous tetrahydrofuran (50 milliliters) in a 250 milliliter round bottom flask. The mixture was then refluxed for 12 hours and the solvent was removed by evaporation. The crude product thus obtained was purified by flash chromatography on silica gel using hexane as eluent to provide 3.1 grams of 2,5-bis(2-thienyl)-3,4-dioctylthiophene.

Workup

  1. temperatureThe mixture was then refluxed for 12 hours
  2. customthe solvent was removed by evaporation
  3. customThe crude product thus obtained
  4. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-523c8e09d4d1408eb42352ff35cdf1b8
Source dataset
uspto-grants-2006_09
Patent number
US07112649B2

Reaction notes

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