Potassium Carbonate → 2,4-Dibromo-5-(2-fluoro-4-nitrophenoxy)benzaldehyde

HRID 1661973Notes

Reaction equation

HRID 1661973 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([Br:10])[C:7]([OH:11])=[CH:6][C:3]=1[CH:4]=[O:5].F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=1[F:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[C:8]([Br:10])[C:7]([O:11][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=2[F:22])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 43035352,4-Dibromo-5-hydroxybenzaldehyde

Product 1

HCID 866384722,4-Dibromo-5-(2-fluoro-4-nitrophenoxy)benzaldehydeYield 70.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4-Dibromo-5-hydroxy-benzaldehyde (50 g, 178.6 mmol), 1,2-difluoro-4-nitrobenzene (28.4 g, 178.6 mmol) and potassium carbonate (49.0 g, 357.2 mmol) are stirred in DMF (500 mL) at 60° C. for 2 hours. The reaction is quenched with water (1000 mL) and extracted with methyl tert-butylether (MTBE) (2×500 mL). The organic layer is washed with saturated sodium chloride aqueous solution (2×500 mL), dried with anhydrous sodium sulfate, and concentrated to obtain a yellow solid. The crude solid is recrystallized in EtOAc/PE (1:5) to give 2,4-dibromo-5-(2-fluoro-4-nitrophenoxy)benzaldehyde as a yellow solid (52.8 g, 70.6% yield).

Workup

  1. customThe reaction is quenched with water (1000 mL)
  2. extractionextracted with methyl tert-butylether (MTBE) (2×500 mL)
  3. washThe organic layer is washed with saturated sodium chloride aqueous solution (2×500 mL)
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto obtain a yellow solid
  7. customThe crude solid is recrystallized in EtOAc/PE (1:5)

Sources & evidence

ORD record
ord-031c0c7685b648cbad77b624f70de529
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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