Benzenediazonium, 3-chloro-, chloride → m-Toluenediazonium chloride

HRID 462490Notes

Reaction equation

HRID 462490 reaction equation
[Cl-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]#[N:10])=[CH:5][CH:4]=1.[Cl-].Cl[C:13]1C=C([N+]#N)C=CC=1>>[Cl-:2].[C:8]1([CH3:13])[CH:3]=[CH:4][CH:5]=[C:6]([N+:9]#[N:10])[CH:7]=1

Participants

3

Reactant 2

HCID 10329810Benzenediazonium, 3-chloro-, chlorideHCID 11819533Benzenediazonium, 4-chloro-, chloride

Product 1

HCID 11829668m-Toluenediazonium chloride

Procedure

When these processes are repeated using variously substituted aryldiazonium salts, very variable yields of between 40 and 85% of theory are obtained. For example, p-chlorobenzenediazonium chloride gives 43%, m-chlorobenzenediazonium chloride gives 36%, m-toluenediazonium chloride gives 69%, o-chlorobenzenediazonium chloride gives 36%, p-dimethylaminobenzenediazonium chloride gives 54%, p-carbamoylbenzenediazonium chloride gives 58%, benzenediazonium chloride gives 72%, p-methoxybenzenediazonium chloride gives 80% and p-sulfobenzenediazonium chloride gives 10 to 20% of the corresponding diazosulfonate.

Workup

  1. customvery variable yields of between 40 and 85% of theory
  2. customare obtained

Sources & evidence

ORD record
ord-9294cf4daf074f6bb93834a22e447873
Source dataset
uspto-grants-1985_05
Patent number
US04515940

Reaction notes

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