Nitric Acid → 5-Bromo-2-nitrobenzaldehyde

HRID 1037519Notes

Reaction equation

HRID 1037519 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]>>[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

3

Reactant 2

HCID 944Nitric AcidHCID 765833-Bromobenzaldehyde

Product 1

HCID 972335-Bromo-2-nitrobenzaldehydeYield 48%

Procedure

To an ice cold conc. sulphuric acid (400 mL) was added fuming nitric acid (200 mL) and to this solution was added 3-bromobenzaldehyde (i) (100 g, 0.540 mol) dropwise within 15 min. The reaction mixture was stirred for 10 min at same temperature at which time TLC showed complete reaction. The reaction mixture was quenched in ice water and filtered to afford a mixture of products which was purified by flash column chromatography eluting with EtOAc/hexane (1-5%) to give 5-bromo-2-nitrobenzaldehyde (ii) as white solid (60 g, 48%).

Workup

  1. customreaction
  2. customThe reaction mixture was quenched in ice water
  3. filtrationfiltered
  4. customto afford
  5. additiona mixture of products which
  6. customwas purified by flash column chromatography
  7. washeluting with EtOAc/hexane (1-5%)

Sources & evidence

ORD record
ord-f6200977730447debd96d25cc6598392
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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