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Azobisisobutyronitrile → Methyl 2-(1-bromoethyl)benzoate

HRID 480554
Notes
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Reaction equation

HRID 480554 reaction equation
[Br:1]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:21]([C:23]1[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26])[CH3:22]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH:21]([C:23]1[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26])[CH3:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 583295Methyl 2-ethylbenzoate

Product 1

HCID 15870654Methyl 2-(1-bromoethyl)benzoateYield 82.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

N-Bromosuccinimide (10.7 g) and azodiisobutyronitrile (catalytic) were added to a solution of methyl 2-ethylbenzoate (10 g) in carbon tetrachloride (50 ml), and the resulting mixture was heated at 80° C. for 6 hours under reflux. After cooling, the reaction mixture was filtered and the filtrate was concentrated to give methyl 2-(1-bromoethyl)benzoate (12 g), almost pure by GC and NMR, as a yellow oil.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-03fa7aaa45b147b7af762b66e71acd3f
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06653258B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes