Malonic Acid → 3-Amino-3-(3-bromo-5-fluorophenyl)propanoic acid

HRID 526359Notes

Reaction equation

HRID 526359 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=O.[C:11]([OH:17])(=[O:16])[CH2:12]C(O)=O.C([O-])(=O)C.[NH4+:22]>C(O)C>[NH2:22][CH:5]([C:4]1[CH:7]=[C:8]([F:10])[CH:9]=[C:2]([Br:1])[CH:3]=1)[CH2:12][C:11]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 517165Ammonium AcetateHCID 219862463-Bromo-5-fluorobenzaldehyde

Product 1

HCID 712589843-Amino-3-(3-bromo-5-fluorophenyl)propanoic acidYield 14.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.72 g (23.25 mmol) 3-bromo-5-fluorobenzaldehyde were suspended in 10 ml ethanol. 2.42 g (23.25 mmol) propanedioic acid and 3.76 g (48.82 mmol) ammonium acetate were added. The mixture was refluxed for 5 hours and after cooling to room temperature filtrated. The residue was washed with cold ethanol and dried in vacuum at 30° C. to give 880 mg (13%) 3-amino-3-(3-bromo-5-fluorophenyl)propionic acid. The filtrate was concentrated and crystallized from ethanol to give further 706 mg (12%) 3-amino-3-(3-bromo-5-fluorophenyl) propionic acid.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. filtrationfiltrated
  3. washThe residue was washed with cold ethanol
  4. customdried in vacuum at 30° C.

Sources & evidence

ORD record
ord-53ea2fee732541a49545744e4a4354ef
Source dataset
uspto-grants-2016_05
Patent number
US09345793B2

Reaction notes

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