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

HRID 2423497Notes

Reaction equation

HRID 2423497 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[Br:10].[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[Br:10][C:3]1[C:2]([F:1])=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:5]([CH:4]=1)[CH:6]=[O:7]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 113796385-Bromo-4-fluoro-2-nitrobenzaldehydeYield 73%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-Fluoro-3-bromo-benzaldehyde (3.00 g, 14.78 mmol) was added to a stirred solution of concentrated nitric acid (67%, 2.02 mL, 29.55 mmol) in concentrated sulfuric acid (18 mL) at 0° C. After the addition was complete, the ice bath was removed and the reaction was allowed to stir for 3 hours at room temperature. Then, the mixture was poured into ice and extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:9 ethyl acetate:hexanes to give 2.66 g (73%) of 5-bromo-4-fluoro-2-nitro-benzaldehyde as a solid. 1H NMR (400 MHz, d6-DMSO): δ 10.14 (s, 1H), 8.31 (d, J=8 Hz, 1H), 8.25 (d, J=7 Hz, 1H).

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. additionThen, the mixture was poured into ice
  4. extractionextracted with diethyl ether
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with 1:9 ethyl acetate

Sources & evidence

ORD record
ord-0930201b3195440f863310fd1a8a0914
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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