Azobisisobutyronitrile → HCID 20513445, compound

HRID 1163999Notes

Reaction equation

HRID 1163999 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])(=[O:3])[CH3:2].[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:10]([CH2:11][Br:20])=[CH:9][CH:8]=[CH:7][C:6]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 20513482HCID 20513482, compound

Product 1

HCID 20513445HCID 20513445, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-chlorophenyl 2-acetoxy-3-methylphenyl ether (17 g), N-bromosuccinimide (13 g) and 2,2'-azobisisobutyronitrile (1.7 g) in benzene (150 ml) was refluxed under heating for 3 hours. After cooling, the precipitate was filtered off. The filtrate was washed with water, aqueous sodium thiosulfate and water successively, dried over magnesium sulfate and then evaporated to give oily 2-chlorophenyl 2-acetoxy-3-bromomethylphenyl ether (22.4 g).

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 3 hours
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered off
  5. washThe filtrate was washed with water, aqueous sodium thiosulfate and water successively
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-d78fd50eea7741ffa4454ce4a1ac116f
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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