Trimethyltin chloride → (Thiene-2,5-diyl)bis(trimethylstannane)

HRID 1796876Notes

Reaction equation

HRID 1796876 reaction equation
C([Li])CCC.Br[C:7]1[CH:11]=[CH:10][S:9][C:8]=1Br.[CH3:13][Sn:14](Cl)([CH3:16])[CH3:15]>O1CCCC1>[CH3:13][Sn:14]([CH3:16])([CH3:15])[C:8]1[S:9][C:10]([Sn:14]([CH3:16])([CH3:15])[CH3:13])=[CH:11][CH:7]=1

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 765902,3-DibromothiopheneHCID 178418339Butyllithium

Product 1

HCID 12841052(Thiene-2,5-diyl)bis(trimethylstannane)Yield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After 18.4 mL (30 mmol) of n-butyl lithium solution (n-BuLi, 1.63M in hexane) was added to a solution of 3.0 g (12.4 mmol) dibromothiophene in tetrahydrofuran (50 mL) at −50° C. under nitrogen atmosphere, the reaction was allowed to proceed for 30 minutes. To the mixture was added 5 g of trimethylstannyl chloride (SnMe3Cl, 25 mmol) and the reaction was continued at −50° C. for about 4˜5 hours. Next, the aqueous layer and organic layer were separated. The obtained organic layer was dried over a drying agent, and then solvents were removed. The resulting crude product was recrystallized from ether twice to afford 3.1 g (yield: 60%) of the title compound as a white crystal.

Workup

  1. waitthe reaction was continued at −50° C. for about 4˜5 hours
  2. customNext, the aqueous layer and organic layer were separated
  3. customThe obtained organic layer was dried over a drying agent
  4. customsolvents were removed
  5. customThe resulting crude product was recrystallized from ether twice

Sources & evidence

ORD record
ord-ee8fe7784fa4432ab563fe0d3f3b1936
Source dataset
uspto-grants-2006_04
Patent number
US07030409B2

Reaction notes

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