Sulfuric Acid → HCID 18785191, compound

HRID 1108515Notes

Reaction equation

HRID 1108515 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([Mg]Cl)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C1COCC1.[CH:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[C:22](Br)[CH:21]=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:26][C:25]1[CH:20]=[CH:21][C:22]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:8][CH:9]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 7806p-BromochlorobenzeneHCID 178420647HCID 178420647, compound

Product 1

HCID 18785191HCID 18785191, compound

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-n-pentoxyphenylmagnesium 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 0.0025 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%, selectivitity 97%). The organic phase is freed from the solvent by distillation. The 4-chloro-4'-pentoxybiphenyl 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-4ebd9fa9764942cfa0692b99c999d926
Source dataset
uspto-grants-2000_05
Patent number
US06066766

Reaction notes

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