Nitric Acid → 5-Bromo-2-nitrobenzaldehyde

HRID 2423502Notes

Reaction equation

HRID 2423502 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O.C(OCC)C>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:4]([CH:3]=1)[CH:5]=[O:6]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 765833-Bromobenzaldehyde

Product 1

HCID 972335-Bromo-2-nitrobenzaldehyde

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

3-Bromo-benzaldehyde (18.50 g, 99.99 mmol) was added to a stirred solution of concentrated nitric acid (70%, 13.09 mL, 199.98 mmol) in concentrated sulfuric acid (125 mL) at 0° C. After the addition was complete, the ice bath was removed and the reaction was allowed to stir for 5 hours at room temperature. Then, the mixture was poured into ice and the solid was collected by filtration. The filtrate was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was combined with the solid previously obtained via the first filtration and dissolved in diethyl ether. Hexanes were added and after crystallization 14.66 g (64%) of 5-bromo-2-nitro-benzaldehyde was collected by filtration and drying. 1H NMR (400 MHz, d6-DMSO): δ 10.19 (s, 1H), 8.10 (s, 2H), 8.02 (s, 1H).

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. additionThen, the mixture was poured into ice
  4. filtrationthe solid was collected by filtration
  5. extractionThe filtrate was extracted with diethyl ether
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompreviously obtained via the first filtration
  10. customafter crystallization 14.66 g (64%) of 5-bromo-2-nitro-benzaldehyde
  11. filtrationwas collected by filtration
  12. customdrying

Sources & evidence

ORD record
ord-2567ccf3abc44bdf991d167f6ad32b91
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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