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

HRID 1011651Notes

Reaction equation

HRID 1011651 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[CH:3]=1.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14]>CN(C)C1C=CN=CC=1.CN(C=O)C.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:12][C:13]([OH:15])=[O:14])=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 2

HCID 867Malonic AcidHCID 1435174-Bromo-2-fluorobenzaldehyde

Product 1

HCID 6883133-(4-Bromo-2-fluorophenyl)-2-propenoic acidYield 85%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromo-2-fluorobenzaldehyde (12.4 g, 61 mmol), malonic acid (12.7 g, 122 mmol) and 4-dimethylamino pyridine (0.75 g, 6.1 mmol) in 20 mL of DMF was heated at 100 degrees Celsius for 2 hrs. After cooling, the reaction mixture was diluted with 300 mL water, and filtered. The solid was collected, and triturated in hexane. The solid was collected and dried in vacuum to give 12.7 g (85%) of a white solid. MS: calc'd 243 (M−H), exp 243 (M−H).

Workup

  1. temperaturewas heated at 100 degrees Celsius for 2 hrs
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. customThe solid was collected
  5. customtriturated in hexane
  6. customThe solid was collected
  7. customdried in vacuum

Sources & evidence

ORD record
ord-bfad1528cb984662ac2c2e3b056a0998
Source dataset
uspto-grants-2011_07
Patent number
US07977372B2

Reaction notes

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