2-Chloro-1-iodo-4-nitrobenzene → 2-Chloro-4-nitrobenzotrifluoride

HRID 1249864Notes

Reaction equation

HRID 1249864 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1I.C[Si](C)(C)[C:14]([F:17])([F:16])[F:15].[F-].[K+]>CN(C)C=O.C(OCC)C.[Cu]I>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[C:14]([F:17])([F:16])[F:15]

Participants

7

Reactant 3

HCID 966402-Chloro-1-iodo-4-nitrobenzeneHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilane

Product 1

HCID 27789852-Chloro-4-nitrobenzotrifluoride

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-chloro-4-iodo-nitrobenzene (2.26 g), trimethyl(trifluoromethyl)silane (5.68 g), copper(I) iodide (2.28 g), and potassium fluoride (0.56 g) in N,N-dimethylformamide (8 mL) is heated in a sealed tube to 80° C. for 40 hours. The solution is then cooled, diluted with diethyl ether, filtered through diatomaceous earth, and the filtrate is washed successively with water, saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure and the residue is chromatographed over silica gel (1% diethyl ether in hexanes followed by 10% ethyl acetate in hexanes is used as the eluant) to provided the desired product as a colorless oil.

Workup

  1. temperatureThe solution is then cooled
  2. filtrationfiltered through diatomaceous earth
  3. washthe filtrate is washed successively with water, saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is chromatographed over silica gel (1% diethyl ether in hexanes

Sources & evidence

ORD record
ord-7c94974826494364887ed4377befed7f
Source dataset
uspto-grants-2002_01
Patent number
US06335350B1

Reaction notes

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