Iodopentafluoroethane → HCID 22931943, compound

HRID 2373337Notes

Reaction equation

HRID 2373337 reaction equation
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH:9]([CH3:14])[CH2:10][CH:11]([CH3:13])[CH3:12])[CH:3]=1.[F:15][C:16](I)([F:21])[C:17]([F:20])([F:19])[F:18]>[Cu].CS(C)=O>[CH3:14][CH:9]([C:4]1[CH:3]=[C:2]([C:16]([F:21])([F:15])[C:17]([F:20])([F:19])[F:18])[CH:8]=[CH:7][C:5]=1[NH2:6])[CH2:10][CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 9636IodopentafluoroethaneHCID 22931936HCID 22931936, compound

Product 1

HCID 22931943HCID 22931943, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

4-Iodo-2-(1,3-dimethylbutyl)aniline (1.35 g, 4.45 mmol), copper powder (0.85 g, 13.4 mmol) and pentafluoroethyl iodide (1.42 g, 5.77 mmol) were added to dimethyl sulfoxide (10 ml), and the resulting mixture was stirred at 130° C. for 4 hours. The mixture was filtered through Celite and the filtrate was diluted with ethyl acetate and washed 4 times with water. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure to obtain 1.24 g of the desired compound.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed 4 times with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c660b32cce024f54839c2021ebc7698b
Source dataset
uspto-grants-2008_12
Patent number
US07459477B2

Reaction notes

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