2-Bromothiophene → 2,2':5',2'',5'',2'''-Quaterthiophene

HRID 523136Notes

Reaction equation

HRID 523136 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:10][C:9]([C:11]2[S:12][C:13]([Sn](CCCC)(CCCC)CCCC)=[CH:14][CH:15]=2)=[CH:8][CH:7]=1)CCC.Br[C:38]1[S:39][CH:40]=[CH:41][CH:42]=1>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:39]1[CH:40]=[CH:41][CH:42]=[C:38]1[C:9]1[S:10][C:6]([C:13]2[S:12][C:11]([C:9]3[S:10][CH:6]=[CH:7][CH:8]=3)=[CH:15][CH:14]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 138512-BromothiopheneHCID 10533055Agn-PC-0N63KQ

Product 1

HCID 3954932,2':5',2'',5'',2'''-QuaterthiopheneYield 141.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

5,5′-bis(tributylstannyl)-2,2′-bithiophene (2.16 g, 2.90 mmol) was dissolved in dry DMF (45 mL) and transferred via cannula to Pd(PPh3)4 (0.101 g, 0.087 mmol) in a Schlenk flask. 2-bromothiophene (1.14 g, 6.96 mmol) was added via syringe and the solution was degassed with nitrogen. Reaction was then heated to 90° C. for 18 hours. Reaction was quenched with water, extracted with chloroform (3×), and the combined organics washed with brine. Organics were dried with magnesium sulfate and concentrated by rotary evaporator yielding crude material as a waxy orange solid. The solid was recrystallized from boiling toluene and collected by filtration. Filtered solid was then redissolved in boiling chloroform and stirred with activated charcoal for 15 minutes. The charcoal was removed by filtering through celite and the chloroform removed by rotary evaporator to yield product as a yellow solid (0.676 g, 2.05 mmol, 70%). Characterization data matches literature. Z. H. Li, et al., Org. Lett. 9:3659-3662 (2007).

Workup

  1. customthe solution was degassed with nitrogen
  2. customReaction
  3. customReaction
  4. customwas quenched with water
  5. extractionextracted with chloroform (3×)
  6. washthe combined organics washed with brine
  7. dry with materialOrganics were dried with magnesium sulfate
  8. concentrationconcentrated by rotary evaporator
  9. customyielding crude material as a waxy orange solid
  10. customThe solid was recrystallized
  11. filtrationcollected by filtration
  12. filtrationFiltered solid
  13. dissolutionwas then redissolved
  14. customThe charcoal was removed
  15. filtrationby filtering through celite
  16. customthe chloroform removed by rotary evaporator

Sources & evidence

ORD record
ord-0a1ac37c5f55435ca98c28bc2981733d
Source dataset
uspto-grants-2016_05
Patent number
US09334304B2

Reaction notes

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