Bromobenzene → Biphenyl

HRID 2397600Notes

Reaction equation

HRID 2397600 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[Na+].[OH-].[Na+]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[Pd].O>[C:2]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7961BromobenzeneHCID 14798Sodium HydroxideHCID 2723810Sodium Formate2×

Product 1

HCID 7095BiphenylYield 66.2%

Reagents, catalysts & solvents 3

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Bromobenzene (15.7 parts), cetyltrimethylammonium bromide (4.0 parts), 3% palladium on charcoal (50% paste; 2.0 parts), sodium formate (6.8 parts) and sodium hydroxide liquor (32%; 27 parts) in water (60 parts) are stirred at the boil under reflux for 4 hours. Sodium formate (6.8 parts) is then added and the mixture held at the boil under reflux for a further 18 hours. The mixture is then steam distilled. The steam distillate is extracted with chloroform (3 × 50 parts) and then the extract dried over anhydrous magnesium sulphate. After filtering off the drying agent the solvent is removed under vacuum to give 5.1 parts (66.2%) of biphenyl.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureunder reflux for a further 18 hours
  3. distillationsteam distilled
  4. extractionThe steam distillate is extracted with chloroform (3 × 50 parts)
  5. dry with materialthe extract dried over anhydrous magnesium sulphate
  6. filtrationAfter filtering off the drying agent the solvent
  7. customis removed under vacuum

Sources & evidence

ORD record
ord-fda8aa9e8def41fc98af88b9a075c68c
Source dataset
uspto-grants-1977_05
Patent number
US04022795

Reaction notes

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