3-Chlorobenzaldehyde → 5-Chloro-2-nitrobenzaldehyde

HRID 1487190Notes

Reaction equation

HRID 1487190 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[N+:10]([O-])([O-:12])=[O:11].[K+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:4]([CH:3]=1)[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 114773-ChlorobenzaldehydeHCID 24434Potassium Nitrate

Product 1

HCID 811235-Chloro-2-nitrobenzaldehydeYield 60.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3-Chlorobenzaldehyde (15 g, 107 mmol) was added to concentrated sulfuric acid (150 mL) at −20° C., followed by addition of potassium nitrate (11.9 g, 117 mmol) in portions, keeping the temperature below −10° C. After addition, the mixture was stirred for 30 minutes and then poured into ice-water. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, washed by brine, dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product 5-chloro-2-nitrobenzaldehyde (12.0 g, yield 60.6%).

Workup

  1. customthe temperature below −10° C
  2. additionAfter addition
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washwashed by brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-6fcefbb227d447e186b16c14c0081945
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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