Azobisisobutyronitrile → HCID 20526235, compound

HRID 1702630Notes

Reaction equation

HRID 1702630 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[O:4][CH:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7].[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[Br:16][C:5]([O:4][C:3]1[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:2]=1[Cl:1])([CH3:10])[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 90988Dichlorprop-methyl

Product 1

HCID 20526235HCID 20526235, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

37.5 parts of methyl 2-(2',4'-dichlorophenoxy)-propionate and 26.7 parts of N-bromosuccinimide in 300 parts of carbon tetrachloride are boiled under reflux, 0.1 part of azo-bis-isobutyronitrile being added every 45 minutes. The mixture is refluxed until the succinimide formed floats on the solvent. A total reaction time of 10 hours is required. The mixture is then cooled to 0° C. and filtered, and the filtrate is concentrated under reduced pressure. 36.9 parts (82% of theory) of methyl 2-bromo-2-(2',4'-dichlorophenoxy)-propionate, of nD22 =1.5395, are obtained.

Workup

  1. temperatureunder reflux
  2. customA total reaction time of 10 hours
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-4561dcefe5cb444dbc16d4df8ccfb818
Source dataset
uspto-grants-1982_09
Patent number
US04348534

Reaction notes

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