Nitric Acid → 5-Bromo-4-fluoro-2-nitrobenzaldehyde

HRID 1357742Notes

Reaction equation

HRID 1357742 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6].[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[C:4]([CH:3]=1)[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 3-bromo-4-fluorobenzaldehyde (5.00 g, 24.6 mmol) in sulfuric acid (25 mL) at 0 ° C. was added dropwise fuming nitric acid (3 mL) in sulfuric acid (30 mL), stirred at room temperature overnight, poured onto ice, the precipitate collected, washed with water, and dried. The crude product was purified by flash chromatography over silica gel eluting with ethylacetate/hexane (3:7) to provide 3.9 g of the title compound as yellow crystals.

Workup

  1. additionpoured onto ice
  2. customthe precipitate collected
  3. washwashed with water
  4. customdried
  5. customThe crude product was purified by flash chromatography over silica gel eluting with ethylacetate/hexane (3:7)

Sources & evidence

ORD record
ord-abd7f12ddcbd456192aa7d11f9e84bd7
Source dataset
uspto-grants-2003_07
Patent number
US06593335B1

Reaction notes

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