2-(Tri-n-butylstannyl)thiophene → HCID 22634037, compound

HRID 1250936Notes

Reaction equation

HRID 1250936 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)CCC.[CH2:19]([O:21][C:22](=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=1)[CH3:20]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[S:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[C:27]1[CH:28]=[CH:29][C:24]([CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:31])=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 7020609Ethyl 2-(4-bromophenyl)acetate

Product 1

HCID 22634037HCID 22634037, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Nitrogen was bubbled through a mixture of 2-tributylstannyl thiophene (15.68 ml, 49.4 mmol) and ethyl(4-bromophenyl)acetate (6 g, 24.7 mmol) in toluene (250 ml) before 0.5 g of tetrakis (triphenylphosphine) palladium (0) was added. The mixture was heated at reflux under nitrogen for 4 hours before it was filtered through magnesol and concentrated. The residue was purified using silica-gel column chromatography by eluting it with 20% ethyl acetate: hexane solution. Ethyl [4-(2-thienyl)phenyl]acetate was isolated as a yellow oil (4.15 g). Yield 68%; MS: 247.5 (M+H)+

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureat reflux under nitrogen for 4 hours before it
  4. filtrationwas filtered through magnesol
  5. concentrationconcentrated
  6. customThe residue was purified
  7. washby eluting it with 20% ethyl acetate

Sources & evidence

ORD record
ord-2dca9875044d48ef8b56136c9d97366b
Source dataset
uspto-grants-2002_01
Patent number
US06340691B1

Reaction notes

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