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

HRID 56462Notes

Reaction equation

HRID 56462 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[F:14])[CH:9]=[O:10]>S(=O)(=O)(O)O>[Br:5][C:6]1[C:13]([F:14])=[CH:12][C:11]([N+:1]([O-:4])=[O:2])=[C:8]([CH:7]=1)[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 113796385-Bromo-4-fluoro-2-nitrobenzaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of concentrated nitric acid (6.8 mL, 101.0 mmol) in concentrated sulfuric acid (60 mL) was slowly added 3-bromo-4-fluorobenzaldehyde (10 g, 49.5 mmol) at 0° C. After the addition was completed, the ice bath was removed, and the reaction was allowed to warm to room temperature and stirred for 3 hours. The mixture was poured into ice water and extracted with ethyl acetate (200 mL). The organic layer was concentrated to give the title compound as a yellow solid (crude, 12 g, 100%), which was used directly for the next step without further purification.

Workup

  1. customat 0° C
  2. additionAfter the addition
  3. customthe ice bath was removed
  4. additionThe mixture was poured into ice water
  5. extractionextracted with ethyl acetate (200 mL)
  6. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-256afc511845463f9e3d6accd8223308
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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