Azobisisobutyronitrile → Methyl 2-bromo-2-(3-methoxyphenyl)acetate

HRID 530609Notes

Reaction equation

HRID 530609 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1.[Br:14]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>ClC(Cl)(Cl)Cl>[Br:14][CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)[C:3]([O:2][CH3:1])=[O:13]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 519609Methyl 2-(3-methoxyphenyl)acetate

Product 1

HCID 289522Methyl 2-bromo-2-(3-methoxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5 g (27.74 mmol) of methyl(3-methoxyphenyl)acetate, 5.2 g (29.14 mmol) of N-bromosuccinimide and a catalytic amount of AIBN in tetrachloromethane (50 ml) was heated under reflux with stirring for 2 h. The cooled reaction solution was filtered and washed with a small volume of dichloromethane. The combined filtrate and wash was concentrated in vacuo to afford methyl 2-bromo-2-(3-methoxyphenyl)acetate as an oil. Used as is in the next step.

Workup

  1. temperatureunder reflux
  2. customThe cooled reaction solution
  3. filtrationwas filtered
  4. washwashed with a small volume of dichloromethane
  5. washThe combined filtrate and wash
  6. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-e01b17d6ede844c3a145971f4c629f5e
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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