Hydrochloric Acid → 3-(4-Bromothiophen-2-yl)acrylic acid

HRID 1931440Notes

Reaction equation

HRID 1931440 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[S:5][CH:6]=1.C(O)(=O)[CH2:10][C:11]([OH:13])=[O:12].N1CCCCC1.Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:10][C:11]([OH:13])=[O:12])[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 877924-Bromothiophene-2-carbaldehyde

Product 1

HCID 27744523-(4-Bromothiophen-2-yl)acrylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

25 g (131 mmol) of 4-bromo-thiophene-2-carbaldehyde were dissolved in 180 ml of pyridine, and 16.34 g (157 mmol) of malonic acid and 1.11 g (13.1 mmol) of piperidine were added. The reaction mix was boiled under reflux for 6 h. After cooling to room temperature, the mixture was poured onto a mixture of ice and concentrated hydrochloric acid. The precipitated product was isolated by filtration. Yield: 21.15 g.

Workup

  1. additionThe reaction mix
  2. temperatureunder reflux for 6 h
  3. customThe precipitated product was isolated by filtration

Sources & evidence

ORD record
ord-1c627d4745b24bd2a8a83ed4d2c46546
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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