Benzene → Biphenyl

HRID 1634247Notes

Reaction equation

HRID 1634247 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:7]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 241BenzeneHCID 10340Sodium Carbonate

Product 1

HCID 7095Biphenyl

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

The residue was dissolved in benzene and then there was added tetrabutylammonium bromide, aqueous Na2CO3 and 2-(tert-butylaminosulfonyl)phenylboronic. This solution was degassed with a stream of nitrogen for 30 minutes. Following the purge, tetrakis(triphenylphosphine)palladium(0) was added and the solution was stirred overnight at reflux. The solution was diluted with EtOAc and washed twice with brine and the organics dried over MgSO4, filtered and the volatiles removed under reduced pressure. The residue was purified by column chromatography (elution with 1:1 hexane/EtOAc) to afford an intermediate biphenyl compound.

Workup

  1. customThis solution was degassed with a stream of nitrogen for 30 minutes
  2. additionwas added
  3. temperatureat reflux
  4. additionThe solution was diluted with EtOAc
  5. washwashed twice with brine
  6. dry with materialthe organics dried over MgSO4
  7. filtrationfiltered
  8. customthe volatiles removed under reduced pressure
  9. customThe residue was purified by column chromatography (elution with 1:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-8a2dfa75b30c472388fb4ad94f9403b8
Source dataset
uspto-grants-2003_01
Patent number
US06506771B2

Reaction notes

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