Malonic Acid → 3-(3-Bromo-4-fluorophenyl)-2-propenoic acid

HRID 2207878Notes

Reaction equation

HRID 2207878 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1CCCCC1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:12][C:13]([OH:15])=[O:14])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 6883113-(3-Bromo-4-fluorophenyl)-2-propenoic acidYield 54.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

3-Bromo-4-fluoro-benzaldehyde (5.0 g, 24.6 mmol), malonic acid (5.6 g, 53.7 mmol), and piperidine (0.5 mL, 4.9 mmol) were added to pyridine (11.4 mL). The reaction mixture was stirred at 100° C. for 3 hours and then concentrated under reduced pressure. Distilled water was added to the reaction mixture, which was then filtered. The resulting solid was recrystallized from ethanol to give 3.3 g of the titled compound as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionDistilled water was added to the reaction mixture, which
  3. filtrationwas then filtered
  4. customThe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-d292ac838ee14bf5a46b97a9cfb067ee
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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