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

HRID 506848Notes

Reaction equation

HRID 506848 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]>OS(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 (5.0 g, 24.6 mmol) in H2SO4 (25 mL) at 0° C. was added nitric acid (3 mL) in H2SO4 (30 mL), dropwise. The resulting mixture was warmed to room temperature overnight. The resulting solution was then poured slowly over ice and filtered to collect the yellow precipitate. The precipitate was washed with H2O and dried, then purified by silica gel chromatography eluted with a solvent mixture of ethyl acetate and heptanes from 0:100 to 25:75 to yield a light yellow solid.

Workup

  1. additionThe resulting solution was then poured slowly over ice
  2. filtrationfiltered
  3. customto collect the yellow precipitate
  4. washThe precipitate was washed with H2O
  5. customdried
  6. custompurified by silica gel chromatography
  7. washeluted with a solvent mixture of ethyl acetate and heptanes from 0:100 to 25:75
  8. customto yield a light yellow solid

Sources & evidence

ORD record
ord-af68d81b219f4ab7a77db71765b26451
Source dataset
uspto-grants-2010_08
Patent number
US07786116B2

Reaction notes

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