Nitric Acid → 3-Bromo-4-hydroxy-5-nitrobenzaldehyde

HRID 1663384Notes

Reaction equation

HRID 1663384 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[N+:11]([O-])([OH:13])=[O:12]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 763083-Bromo-4-hydroxybenzaldehyde

Product 1

HCID 14943783-Bromo-4-hydroxy-5-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-bromo-4-hydroxy-benzaldehyde (20 g) in acetic acid (200 ml) was added fuming nitric acid (4.18 ml). The resulting suspension was stirred for 3 h. The solid was collected by filtration. Another 420 μl of fuming nitric acid was added to the filtrate. After 45 min., water was added and the resulting precipitate was collected by filtration. The combined solids were washed with water and dried in vacuo.

Workup

  1. filtrationThe solid was collected by filtration
  2. additionAnother 420 μl of fuming nitric acid was added to the filtrate
  3. waitAfter 45 min.
  4. additionwater was added
  5. filtrationthe resulting precipitate was collected by filtration
  6. washThe combined solids were washed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-91bd44bbfa204111add1a3c6ef7a4392
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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