Bromobenzene → Biphenyl

HRID 2397606Notes

Reaction equation

HRID 2397606 reaction equation
[OH-].[Na+].C([O-])=O.[Na+].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[Pd].O>[C:8]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7961BromobenzeneHCID 14798Sodium HydroxideHCID 2723810Sodium Formate2×

Product 1

HCID 7095Biphenyl

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture comprising 4 parts of sodium diisopropyl naphthalene sulphonate, 1.2 parts of 3% palladium on carbon catalyst, 20 parts of sodium hydroxide, 80 parts of water, 6.8 parts of sodium formate and 15.7 parts of bromobenzene is stirred and heated for 4 hours under reflux. The mixture is then allowed to cool to 90°, a further charge of 6.8 parts of sodium formate is added, and the mixture is reheated and stirred under reflux for a further 16 hours. The mixture is then steam distilled until 800 parts of distillate are collected. The distillate is extracted with chloroform and the chloroform solution, is shown by gas chromatography to contain benzene and biphenyl but no bromobenzene. The chloroform solution is then concentrated by distillation, yielding 5.01 parts of biphenyl, melting at 69°-70°.

Workup

  1. temperatureheated for 4 hours
  2. temperatureunder reflux
  3. temperatureto cool to 90°
  4. additionis added
  5. stirringstirred
  6. temperatureunder reflux for a further 16 hours
  7. distillationsteam distilled until 800 parts of distillate
  8. customare collected
  9. extractionThe distillate is extracted with chloroform
  10. concentrationThe chloroform solution is then concentrated by distillation

Sources & evidence

ORD record
ord-b30180fa8de14340b5568122fac5cccd
Source dataset
uspto-grants-1977_05
Patent number
US04022795

Reaction notes

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