Hydrochloric Acid → 3-(5-Bromo-2-thienyl)-2-propenoic acid

HRID 1873756Notes

Reaction equation

HRID 1873756 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.C(O)(=O)[CH2:10][C:11]([OH:13])=[O:12].N1CCCCC1.Cl>N1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[S:6][C:5]([CH:7]=[CH:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 35655923-(5-Bromo-2-thienyl)-2-propenoic acid

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

3 g (15.7 mmol) of 5-bromo-thiophene-2-carbaldehyde were dissolved in 30 ml of pyridine and 1.96 g (18.8 mmol) of malonic acid and 133 mg (1.6 mmol) of piperidine was added. The reaction mixture was boiled under reflux for 6 h. After cooling to room temperature, it was poured into a mixture of ice and concentrated aqueous hydrochloric acid whereupon the product precipitated. The product was isolated by filtration, dissolved in ethyl acetate, and the solution was washed with 0.1 M hydrochloric acid. The organic phase was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure. Yield: 3.0 g.

Workup

  1. temperatureunder reflux for 6 h
  2. customprecipitated
  3. customThe product was isolated by filtration
  4. washthe solution was washed with 0.1 M hydrochloric acid
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-51a806ed9fd44b998a99f275728e939e
Source dataset
uspto-grants-2012_11
Patent number
US08304438B2

Reaction notes

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