4,4'-Dibromobiphenyl → Biphenyl

HRID 2290797Notes

Reaction equation

HRID 2290797 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O.[PH2]([O-])=O.[Na+]>O1CCCC1.[Pd].O>[C:5]1([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1.[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 71104,4'-DibromobiphenylHCID 10340Sodium CarbonateHCID 178418950HCID 178418950, compound

Product 2

HCID 7095BiphenylHCID 71014-Bromobiphenyl

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.1 g of 4,4'-dibromo biphenyl in 30 ml tetrahydrofuran was added 3.5 g sodium carbonate and 400 mg of 5% palladium on carbon. To this reaction mixture there was added 2.5 g sodium hypophosphite monohydrate in about 20 ml water. After about one hour, a GC analysis established that all of the starting material had reacted to yield primarily biphenyl with a trace amount of p-mono-bromobiphenyl.

Workup

  1. customhad reacted

Sources & evidence

ORD record
ord-bdbb6731b94b412e8ae36996f9466339
Source dataset
uspto-grants-1986_10
Patent number
US04618686

Reaction notes

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