Ethyl 2-(2-bromothiophen-3-yl)acetate → HCID 85979007, compound

HRID 2252267Notes

Reaction equation

HRID 2252267 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]>C1COCC1.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>[CH2:11]([O:10][C:8](=[O:9])[CH2:7][C:6]1[CH:5]=[CH:4][S:3][C:2]=1[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1)[CH3:12]

Participants

4

Reactant 1

HCID 67496474Ethyl 2-(2-bromothiophen-3-yl)acetate

Product 1

HCID 85979007HCID 85979007, compoundYield 137.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a dried 250 ml three-neck round-bottom flask containing 50 ml of dry THF containing dichlorobis-(triphenylphosphine)palladium (1.20 g) was cannulated 8.5 grams (34 mmol) of ethyl 2-bromothiophene-3-acetate dissolved in 80 ml of dry THF. The mixture was refluxed for 24 hours. The solvent was removed under vacuum, and the residue was dissolved in CH2Cl2 (100 ml). The solution was washed with water (100 ml×3), and dried with MgSO4. The solvent was evaporated and the residue was purified by column chromatography using silica with toluene as eluent. A total of 5.9 grams of ethyl(2,2′-bithiophene)-3-acetate was obtained as a clear oil resulting in a 69% yield. 1H-NMR (CDCl3): 7.33 (dd, 1H), 7.23 (d, 1H), 7.19 (dd, 1H), 7.08 (dd, 1H), 7.05(d, 1H), 4.17 (q, 2H), 3.75 (s, 2H), 1.27 (t, 3H)

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue was dissolved in CH2Cl2 (100 ml)
  4. washThe solution was washed with water (100 ml×3)
  5. dry with materialdried with MgSO4
  6. customThe solvent was evaporated
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-28fe194b21de401aa4696d617aeb1b2f
Source dataset
uspto-grants-2008_01
Patent number
US07321012B2

Reaction notes

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