Nitric Acid → 5-Bromo-2,4-dinitrobenzaldehyde

HRID 1037520Notes

Reaction equation

HRID 1037520 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[N+:13]([O-])([OH:15])=[O:14]>>[Br:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 972335-Bromo-2-nitrobenzaldehyde

Product 1

HCID 772315365-Bromo-2,4-dinitrobenzaldehyde

Procedure

To ice cold conc. sulphuric acid (360 mL) was added fuming nitric acid (180 mL) and to this solution was added compound (ii) (60 g, 0.26 mol) within 15 min. The reaction mixture was stirred for 10 min at same temperature then at RT for 30 min, at 45° C. for 2 h and finally at 50° C. for 3 h at which time TLC showed complete reaction. The reaction mixture was quenched in ice water and extracted with chloroform to give a mixture of products which was separated by flash column chromatography eluting with EtOAc/hexane (5-30%). The desired 5-bromo-2,4-dinitrobenzaldehyde (iii) was isolated as white solid (5.1 g, 7%).

Workup

  1. waitat RT for 30 min
  2. waitat 45° C. for 2 h
  3. waitfinally at 50° C. for 3 h at which time TLC showed complete
  4. customreaction
  5. customThe reaction mixture was quenched in ice water
  6. extractionextracted with chloroform
  7. customto give
  8. additiona mixture of products which
  9. customwas separated by flash column chromatography
  10. washeluting with EtOAc/hexane (5-30%)

Sources & evidence

ORD record
ord-93953d088bf046089a9146f71dccce43
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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