Trifluoroiodomethane → 1,3-Dimethyl-5-(trifluoromethyl)benzene

HRID 2414169Notes

Reaction equation

HRID 2414169 reaction equation
I[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:10][C:11](I)([F:13])[F:12]>CN(C)C=O.O.[Cu]>[F:10][C:11]([F:13])([F:12])[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 2

HCID 16843TrifluoroiodomethaneHCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 204346091,3-Dimethyl-5-(trifluoromethyl)benzene

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-iodo-m-xylene (2.3 g) in dimethylformamide (DMF) (30 ml) and copper bronze (0.65 g) in a stainless steel tube is cooled and treated with trifluoromethyliodide (15 g). The tube is sealed and heated at 130°-140° C. in a rocking autoclave for 6 hours. After cooling and venting, the reaction mixture is diluted with water and extracted with n-hexane (2×200 ml). The combined hexane extracts are washed with aqueous NaHCO3 and water. After drying over MgSO4, the solvent is removed under reduced pressure. The residue is subjected to chromatography over silica gel to yield purified 5-(trifluoromethyl)-m-xylene.

Workup

  1. customThe tube is sealed
  2. temperatureheated at 130°-140° C. in a rocking autoclave for 6 hours
  3. temperatureAfter cooling
  4. extractionextracted with n-hexane (2×200 ml)
  5. washThe combined hexane extracts are washed with aqueous NaHCO3 and water
  6. dry with materialAfter drying over MgSO4
  7. customthe solvent is removed under reduced pressure
  8. customto yield
  9. custompurified 5-(trifluoromethyl)-m-xylene

Sources & evidence

ORD record
ord-088d0ea13ea84254a19443af5d542c12
Source dataset
uspto-grants-1988_01
Patent number
US04721791

Reaction notes

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