Dimethylformamide → 1,3-Dichloro-2-fluoro-5-nitrobenzene

HRID 1709691

Reaction equation

HRID 1709691 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[C:6]([Cl:9])[C:7]=1Cl.[F-:13].[K+].CN(C)C=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[F:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 883653,4,5-TrichloronitrobenzeneHCID 522689Potassium Fluoride2×

Product 1

HCID 765541,3-Dichloro-2-fluoro-5-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,4,5-trichloronitrobenzene (13.55 g, 59 mmol), potassium fluoride (4.65 g, 80 mmol) and dimethylformamide (DMF; 66 ml) is heated at 140° for 15 hours. An additional 2.5 g of potassium fluoride is added and the mixture is stirred an additional 15 hours at 140°. The reaction mixture is poured into water and extracted with ether. The combined organic layers are washed with water and with brine and filtered, and the solvent is removed to give a dark solid, which is purified by column chromatography to give 3,5-dichloro-4-fluoronitrobenzene, a yellow powder.

Workup

  1. temperatureis heated at 140° for 15 hours
  2. extractionextracted with ether
  3. washThe combined organic layers are washed with water and with brine
  4. filtrationfiltered
  5. customthe solvent is removed
  6. customto give a dark solid, which
  7. customis purified by column chromatography

Sources & evidence

ORD record
ord-3a22b09c30b14d1b975aac63b5bfbd61
Source dataset
uspto-grants-1990_08
Patent number
US04950678

Linked notes

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