Dimethylformamide → Ethyl ([1~2~,2~2~:2~5~,3~2~-terthiophen]-2~3~-yl)acetate

HRID 1525375Notes

Reaction equation

HRID 1525375 reaction equation
Br[C:2]1[S:3][C:4](Br)=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].C([Sn](CCCC)(CCCC)[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)CCC.CN(C=O)C>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.O>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:2]1[S:3][C:4]([C:21]2[S:20][CH:19]=[CH:23][CH:22]=2)=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 11209627HCID 11209627, compound2×

Product 1

HCID 58051793Ethyl ([1~2~,2~2~:2~5~,3~2~-terthiophen]-2~3~-yl)acetateYield 85%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The synthesis of 3T-ET is carried by first synthesizing ethyl 2-(2,5-dibromothiophen-3-yl)acetate using known methods and is performed as follows. Ethyl 2-(2,5-dibromothiophen-3-yl)acetate (6.4 g, 10 mmol) and 2-(tributylstannyl)thiophene (15 g, 20 mmol) are added to a 30 mL dry DMF solution of dichlorobis-(triphenylphosphine)palladium (1.3 g, 1.5 mmol). After three freeze thaw cycles, the mixture is heated at 100° C. for 48 hours. The mixture is cooled to room temperature and poured into a beaker containing 150 mL of water and subsequently extracted with CH2Cl2. The extracted CH2Cl2 mixture is dried with Na2SO4. After filtering and evaporation of solvent, the crude product is purified by chromatography on silica gel using toluene as eluent. The final product is obtained in 85% yield as pale yellow oil. The characterization of the compound is consistent with that published in the literature.

Workup

  1. customThe synthesis of 3T-ET
  2. temperatureThe mixture is cooled to room temperature
  3. additionpoured into a beaker
  4. extractionsubsequently extracted with CH2Cl2
  5. dry with materialThe extracted CH2Cl2 mixture is dried with Na2SO4
  6. filtrationAfter filtering
  7. customevaporation of solvent
  8. customthe crude product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-0bf6c1fb5e05468b95bca37191ae4154
Source dataset
uspto-grants-2015_07
Patent number
US09079999B2

Reaction notes

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