Nitric Acid → 5-Bromo-2-nitrobenzaldehyde

HRID 595697Notes

Reaction equation

HRID 595697 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10]>S(=O)(=O)(O)O>[Br:5][C:6]1[CH:13]=[CH:12][C:11]([N+:1]([O-:4])=[O:2])=[C:8]([CH:7]=1)[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 765833-Bromobenzaldehyde

Product 1

HCID 972335-Bromo-2-nitrobenzaldehydeYield 48%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Fuming nitric acid (200 mL) was added to sulphuric acid (400 mL) at 0° C. and then 3-bromobenzaldehyde (100 g, 0.54 mol) was added dropwise in 15 minutes. After stirring for 10 minutes at the same temperature, the reaction mixture was poured into ice water and filtered to afford the mixture of products which was purified by flash column chromatography eluting with PE/EtOAc (100/1 to 20/1) to give 5-bromo-2-nitrobenzaldehyde as white solid (60 g, 48%). 1H-NMR (CDCl3, 400 MHz) δ 10.41 (s, 1H), 8.02˜8.06 (m, 2H), 7.88 (s, 1H). MS (M+H)+: 230/232.

Workup

  1. filtrationfiltered
  2. customto afford
  3. additionthe mixture of products which
  4. customwas purified by flash column chromatography
  5. washeluting with PE/EtOAc (100/1 to 20/1)

Sources & evidence

ORD record
ord-3c85c18a8659461cbf2eedff12099197
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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