5-Bromo-4-fluoro-2-nitrobenzaldehyde → 2-Amino-5-bromo-4-fluorobenzaldehyde

HRID 1029017Notes

Reaction equation

HRID 1029017 reaction equation
[Br:1][C:2]1[C:3]([F:13])=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([CH:9]=1)[CH:7]=[O:8]>C(Cl)Cl.C1COCC1.[Pt]>[NH2:10][C:5]1[CH:4]=[C:3]([F:13])[C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 1

HCID 113796385-Bromo-4-fluoro-2-nitrobenzaldehyde

Product 1

HCID 181871272-Amino-5-bromo-4-fluorobenzaldehyde

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of Pt/C (10%, 1.5 g, 0.77 mmol) in DCM (200 mL) and THF (50 mL) was added 5-bromo-4-fluoro-2-nitrobenzaldehyde (9.0 g, 36.3 mmol). The mixture was purged with H2 gas, and was stirred under an atmosphere of H2 gas at ambient temperature for 24 h. The reaction mixture was filtered through celite rinsing with DCM. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (600 mL) eluting with 15% EtOAc/hexane to afford 2-amino-5-bromo-4-fluorobenzaldehyde.

Workup

  1. customThe mixture was purged with H2 gas
  2. filtrationThe reaction mixture was filtered
  3. washthrough celite rinsing with DCM
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography on silica gel (600 mL)
  6. washeluting with 15% EtOAc/hexane

Sources & evidence

ORD record
ord-4d1de3985ee24963b36f006593163567
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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