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

HRID 2378539Notes

Reaction equation

HRID 2378539 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].N([O-])=O.[Na+]>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

5

Reactant 3

HCID 944Nitric AcidHCID 763083-Bromo-4-hydroxybenzaldehydeHCID 23668193Sodium Nitrite

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-bromo-4-hydroxybenzaldehyde (6.30 g) in acetic acid (45 ml) was added dropwise with 70% nitric acid (5.85 ml) on a water bath, then added with sodium nitrite (62 mg), and further stirred for 2 hours. The reaction mixture was poured into ice water (300 ml), and precipitates were taken by filtration, and washed with water (50 ml×3). The precipitates were dried under reduced pressure for 24 hours to obtain the title compound (Intermediate 26, 5.88 g).

Workup

  1. customprecipitates
  2. filtrationwere taken by filtration
  3. washwashed with water (50 ml×3)
  4. customThe precipitates were dried under reduced pressure for 24 hours

Sources & evidence

ORD record
ord-b9bb6c5a554b46d597f97b35c0d964bc
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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