Dimethyl Sulfoxide → HCID 14834673, compound

HRID 1722289Notes

Reaction equation

HRID 1722289 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([F:11])=[C:4]([F:12])[C:3]=1[CH3:13].[F-:14].[K+].CS(C)=O>C1C=CC=CC=1>[F:14][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([F:11])=[C:4]([F:12])[C:3]=1[CH3:13]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 522689Potassium FluorideHCID 14834653HCID 14834653, compound

Product 1

HCID 14834673HCID 14834673, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 2-chloro-5,6-difluoro-3-nitrotoluene (1.0 g) are added spray-dried potassium fluoride (1.4 g), anhydrous dimethylsulfoxide (10 ml) and benzene (10 ml), and the moisture is removed by azeotropic distillation together with benzene. Subsequently, the mixture is stirred at 170°-180° C. under argon stream for 3.5 hours. After cooling, the reaction mixture is poured into ice water and extracted with diethyl ether. The extract is washed with water, dried and then the solvent is distilled off. The residue is purified by silica gel column chromatography (solvent, n-hexane) to give 2,5,6-trifluoro-3-nitrotoluene (0.45 g).

Workup

  1. customthe moisture is removed by azeotropic distillation together with benzene
  2. temperatureAfter cooling
  3. additionthe reaction mixture is poured into ice water
  4. extractionextracted with diethyl ether
  5. washThe extract is washed with water
  6. customdried
  7. distillationthe solvent is distilled off
  8. customThe residue is purified by silica gel column chromatography (solvent, n-hexane)

Sources & evidence

ORD record
ord-9f39ab8ffa2447aabf022d9930b31160
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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