Azobisisobutyronitrile → 29610-84-2

HRID 1027957Notes

Reaction equation

HRID 1027957 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1C(=O)N([Br:18])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:1][O:2][CH2:3][CH:4]([Br:18])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 19089(2-Methoxyethyl)benzeneHCID 67184N-bromobutanimide

Product 1

HCID 1135635029610-84-2Yield 84.2%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of methylphenethylether (1.0 g, 7.34 mmol), NBS (1.96 g, 11.01 mmol) and AIBN (240 mg, 1.47 mmol) in carbon tetrachloride (30 ml) was heated under reflux for 2 hours. After cooling, the reaction mixture was diluted with saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The extract was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give a crude 2-methoxy-1-phenylbromoethane (1.33 g, 84%) as brown liquid.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter cooling
  3. extractionextracted with chloroform
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0dba8d26f51f48bc8a4decef938d79e7
Source dataset
uspto-grants-2014_05
Patent number
US08735401B2

Reaction notes

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