Sulfuric Acid → 4-Chloro-3'-bis(trimethylsilyl)aminobiphenyl

HRID 1108516Notes

Reaction equation

HRID 1108516 reaction equation
[CH3:1][Si:2]([N:5]([Si:14]([CH3:17])([CH3:16])[CH3:15])[C:6]1[CH:7]=[C:8]([Mg]Cl)[CH:9]=[CH:10][CH:11]=1)([CH3:4])[CH3:3].C1COCC1.[CH:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[C:25](Br)[CH:24]=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:29][C:28]1[CH:23]=[CH:24][C:25]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([N:5]([Si:14]([CH3:17])([CH3:16])[CH3:15])[Si:2]([CH3:4])([CH3:3])[CH3:1])[CH:7]=2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 7806p-BromochlorobenzeneHCID 178420688HCID 178420688, compound

Product 1

HCID 154517394-Chloro-3'-bis(trimethylsilyl)aminobiphenyl

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 3-bis(trimethylsilyl)aminophenyl-magnesium 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 THF. After stirring under reflux for four hours, the mixture is hydrolyzed with dilute sulfuric acid (conversion 99%, selectivity 97%). The organic phase is freed from the solvent by distillation. The crude 4-chloro-3'-bis(trimethylsilyl)aminobiphenyl thus obtained is recrystallized from isopropanol.

Workup

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

Sources & evidence

ORD record
ord-4b2028f7ecee4ba4a4f922744bc51c69
Source dataset
uspto-grants-2000_05
Patent number
US06066766

Reaction notes

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