Dimethylformamide → 4-Fluoro-3-nitrobenzaldehyde

HRID 1263341Notes

Reaction equation

HRID 1263341 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[F-:13].[K+].CN(C)C=O>O>[F:13][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 855054-Chloro-3-nitrobenzaldehydeHCID 522689Potassium Fluoride

Product 1

HCID 5981294-Fluoro-3-nitrobenzaldehydeYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

93 g (0.5 mol) of 4-chloro-3-nitrobenzaldehyde and 58 g (1 mol) of potassium fluoride are suspended in 250 mol of dimethylformamide. The reaction mixture contains 0.02% of H2O. The mixture is stirred for one hour at 160° C. and the dimethylformamide is evaporated off in vacuo. The residue is cooled and stirred with 200 ml of water, the mixture is extracted with methylene chloride and the organic phase is dried. After the methylene chloride has been evaporated off, 83 g of 4-fluoro-3-nitrobenzaldehyde with a content of 90.2% are obtained.

Workup

  1. customthe dimethylformamide is evaporated off in vacuo
  2. temperatureThe residue is cooled
  3. stirringstirred with 200 ml of water
  4. extractionthe mixture is extracted with methylene chloride
  5. customthe organic phase is dried
  6. customAfter the methylene chloride has been evaporated off

Sources & evidence

ORD record
ord-12465fbdb8a34f8696f5542a5ab32848
Source dataset
uspto-grants-1984_06
Patent number
US04456772

Reaction notes

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