Benzene, 1-iodo-2-(trifluoromethyl)- → 1,1'-Biphenyl, 2,2'-bis(trifluoromethyl)-

HRID 985353Notes

Reaction equation

HRID 985353 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9]>[Cu].CN(C=O)C>[F:9][C:8]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9]

Participants

4

Reactant 1

HCID 67957Benzene, 1-iodo-2-(trifluoromethyl)-

Product 1

HCID 30139061,1'-Biphenyl, 2,2'-bis(trifluoromethyl)-Yield 78.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

To a 2-L three-necked, round-bottom flask fitted with a mechanical stirrer and a condenser was added 507.5 g of 2-iodotrifluoromethylbenzene (1.86 mol), 282.0 g of copper powder and 400 ml of DMF. The reaction mixture was stirred and heated at reflux for 24 hours and filtered. The filtrate was distilled under reduced pressure to yield 211.8 g (78%) of a light yellow oil.

Workup

  1. customTo a 2-L three-necked, round-bottom flask fitted with a mechanical stirrer and a condenser
  2. temperatureheated
  3. temperatureat reflux for 24 hours
  4. filtrationfiltered
  5. distillationThe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-1da025868e374fa18e9c40a21616e6b3
Source dataset
uspto-grants-2005_03
Patent number
US06870978B2

Reaction notes

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