2-(Tri-n-butylstannyl)thiophene → HCID 21881428, compound

HRID 721972Notes

Reaction equation

HRID 721972 reaction equation
Br[C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3Br)[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([Sn]([C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)(CCCC)CCCC)CCC>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.ClCCl>[S:31]1[CH:32]=[CH:33][CH:34]=[C:30]1[C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[C:32]3[S:31][CH:30]=[CH:34][CH:33]=3)[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 15270537HCID 15270537, compound

Product 1

HCID 21881428HCID 21881428, compoundYield 103%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

An airfree tube containing 1,9-dibromothianthrene (187 mg, 0.5 mmole) and Pd(PPh3)2Cl2 (35 mg, 0.05 mmole) was flame dried and filled with Ar. DMF (5 mL) was added to the tube and the tube was heated to 70° C. Tributylstannylthiophene (580 mg, 1.5 mmole) was added and the solution turned black. The reaction mixture was stirred for 2 days and then cooled down to room temperature. It was poured into dichloromethane (50 mL) and the organic layer was washed by water twice, dried by MgSO4. The solvent was removed in vacao. The crude product was further purified by column chromatography (hexane/dichloromethane 6/1) and yield white crystal (196 mg, 92%).

Workup

  1. temperaturewas flame
  2. customdried
  3. additionfilled with Ar
  4. additionDMF (5 mL) was added to the tube
  5. temperaturecooled down to room temperature
  6. washthe organic layer was washed by water twice
  7. dry with materialdried by MgSO4
  8. customThe solvent was removed in vacao
  9. customThe crude product was further purified by column chromatography (hexane/dichloromethane 6/1)

Sources & evidence

ORD record
ord-79d69829726f4db6abdd01cf1bcbc77e
Source dataset
uspto-grants-2006_11
Patent number
US07138075B2

Reaction notes

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