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

HRID 595698Notes

Reaction equation

HRID 595698 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 sulphuric acid (360 mL) was added fuming nitric acid (180 mL). 5-bromo-2-nitrobenzaldehyde (60 g, 0.26 mol) was added to the solution within 15 min. The reaction mixture was stirred for 10 minutes at the 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 poured into ice water and extracted with chloroform to give a mixture of products which was separated by flash column chromatography eluting with PE/EtOAc (20/1 to 3/1). The desired 5-bromo-2,4-dinitrobenzaldehyde was isolated as white solid (6.5 g, 9%). 1H-NMR (CDCl3, 400 MHz) δ 10.48 (s, 1H), 8.61 (s, 1H), 8.30 (s, 1H). MS (M+H)+: 275/277.

Workup

  1. waitat RT for 30 min
  2. waitat 45° C. for 2 h
  3. waitfinally at 50° C. for 3 h
  4. customreaction
  5. extractionextracted with chloroform
  6. customto give
  7. additiona mixture of products which
  8. customwas separated by flash column chromatography
  9. washeluting with PE/EtOAc (20/1 to 3/1)

Sources & evidence

ORD record
ord-b2dc43a4da264159a4a224c17a2d8353
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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