Azobisisobutyronitrile → HCID 20526235, compound

HRID 1702629Notes

Reaction equation

HRID 1702629 reaction equation
BrBr.[Cl:3][C:4]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:5]=1[O:6][CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9].[Br:18]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:18][C:7]([O:6][C:5]1[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:4]=1[Cl:3])([CH3:12])[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 6547Azobisisobutyronitrile2×HCID 24408Bromine2×HCID 67184N-bromobutanimideHCID 90988Dichlorprop-methyl

Product 1

HCID 20526235HCID 20526235, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent3×

Conditions

Temperature
77 °C

Procedure

A saturated aqueous solution of 0.01 part of bromine and one part of carbon tetrachloride is added to a mixture of 37.5 parts of methyl 2-(2',4'-dichlorophenoxy)-propionate, 26.7 parts of N-bromosuccinimide, 0.1 parts of azo-bis-isobutyronitrile and 300 parts of carbon tetrachloride. After 45 minutes of heating, 0.1 part of azo-bis-isobutyronitrile and 0.01 part of bromine in 1 part of carbon tetrachloride are added, at 70° C., and the batch is then stirred for 45 minutes at 77° C. It is then cooled to 40° C. and filtered, and the filtrate is concentrated under reduced pressure. 45 parts (91.5% of theory) of methyl 2-bromo-2-(2',4'-dichlorophenoxy)-propionate, of nD22 =1.5390, are obtained.

Workup

  1. temperatureAfter 45 minutes of heating
  2. temperatureIt is then cooled to 40° C.
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-bc57103fb6394258b3fa9c75a8d84a12
Source dataset
uspto-grants-1982_09
Patent number
US04348534

Reaction notes

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