Nitric Acid → 5-Bromo-2-methoxy-3-nitrobenzaldehyde

HRID 1349939Notes

Reaction equation

HRID 1349939 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 906845-Bromo-2-methoxybenzaldehyde

Product 1

HCID 210937475-Bromo-2-methoxy-3-nitrobenzaldehydeYield 57.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5-Bromo-2-methoxybenzaldehyde (29.65 g, 138 mmol) was added to stirred concentrated sulfuric acid (160 mL) at −15° C. Nitric acid (70% w/w) (16 g) was added dropwise. Further stirring was allowed for 15 mins at this temperature before the mixture was poured onto crushed ice (2 L). The resulting precipitate was collected by filtration and partitioned between dichloromethane (800 mL) and saturated sodium hydrogen carbonate (1 L). The organic layer was dried (Na2SO4) and evaporated in vacuo to give the title compound (20.5 g) as a crude solid.

Workup

  1. additionwas poured
  2. filtrationThe resulting precipitate was collected by filtration
  3. custompartitioned between dichloromethane (800 mL) and saturated sodium hydrogen carbonate (1 L)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-bf32651281b14c6ebabefb440b72bb2d
Source dataset
uspto-grants-2007_05
Patent number
US07214674B2

Reaction notes

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