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

HRID 1828611Notes

Reaction equation

HRID 1828611 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-b8b25c1aa56a4d11a472817993e8beff
Source dataset
uspto-grants-2006_06
Patent number
US07058249B2

Reaction notes

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