Sulfuric Acid → 4,4'-Dichlorobiphenyl

HRID 1108513Notes

Reaction equation

HRID 1108513 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Cl)=[CH:4][CH:3]=1.C1COCC1.[CH:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[C:17](Br)[CH:16]=1.S(=O)(=O)(O)O>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:17]2[CH:16]=[CH:15][C:20]([Cl:21])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 7806p-BromochlorobenzeneHCID 178420682HCID 178420682, compound

Product 1

HCID 163084,4'-Dichlorobiphenyl

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.5 mol of a 25% strength by weight 4-chlorophenylmagnesium chloride/THF solution is added dropwise in the course of 30 minutes to a boiling solution of 0.5 mol of 1,4-bromochlorobenzene and 0.25 g of Pd(dppf)Cl2 *CH2Cl2 in 100 ml of THF. After stirring under reflux for four hours, the mixture is hydrolyzed with dilute sulfuric acid (conversion 99%, selectivity 98%). The organic phase is freed from the solvent by distillation. The crude 4,4'-dichlorobiphenyl thus obtained is recrystallized from ethanol.

Workup

  1. temperatureunder reflux for four hours
  2. distillationThe organic phase is freed from the solvent by distillation

Sources & evidence

ORD record
ord-4e9a7076145b4f1aa26da704fab5abb4
Source dataset
uspto-grants-2000_05
Patent number
US06066766

Reaction notes

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