Trifluoroiodomethane → HCID 18451515, compound

HRID 1270755Notes

Reaction equation

HRID 1270755 reaction equation
I[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[CH:7][CH:8]=2)[CH:3]=1.[F:15][C:16](I)([F:18])[F:17]>N1C=CC=CC=1.[Cu]>[N+:12]([C:6]1[CH:7]=[CH:8][C:9]2[C:4](=[CH:3][C:2]([C:16]([F:18])([F:17])[F:15])=[CH:11][CH:10]=2)[CH:5]=1)([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 16843TrifluoroiodomethaneHCID 184515142-Iodo-7-nitronaphthalene

Product 1

HCID 18451515HCID 18451515, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-iodo-7-nitronaphthalene (1 g, 3.34 mmol), trifluoromethyliodide (0.328 mL, 4.01 mmol) and copper powder (2.55 g, 40.1 mmol) in pyridine (20 mL) in a sealed tube is heated with stirring at 120° C. for 20 hours. After cooling, the reaction mixture is filtered and extracted with EtOAc. The organic extracts are washed with water, 0.1 M citric acid solution and dried (Na2SO4). Concentration and purification of the residual oil by flash chromatography on silica gel (2:1 hexanes/EtOAc) gives 2-nitro-7-trifluoromethylnaphthalene as a yellow solid.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. extractionextracted with EtOAc
  5. washThe organic extracts are washed with water, 0.1 M citric acid solution
  6. dry with materialdried (Na2SO4)
  7. concentrationConcentration and purification of the residual oil by flash chromatography on silica gel (2:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-0e9f8dab1d794e9e9bdb1f3b34dcc48e
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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