Azobisisobutyronitrile → Methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetate

HRID 1609540Notes

Reaction equation

HRID 1609540 reaction equation
[Br:1]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[CH2:21]1[O:29][C:28]2[CH:27]=[CH:26][C:25]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:24][C:23]=2[O:22]1>>[Br:1][CH:30]([C:25]1[CH:26]=[CH:27][C:28]2[O:29][CH2:21][O:22][C:23]=2[CH:24]=1)[C:31]([O:33][CH3:34])=[O:32]

Participants

4

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetate

Product 1

HCID 11821769Methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetate

Procedure

N-Bromosuccinimide (3.95 g, 22.2 mMol) and AIBN (0.098 g, 0.06 mMol) were added to a solution of methyl (3,4-methylenedioxyphenyl)acetate (3.9 g, 21.2 mMol) and the mixture was refluxed for 2.5 h. The reaction was cooled and filtered. The filtrate was concentrated in vacuo and the residue obtained was purified by flash chromatography on silica-gel using 10% ethyl acetate-hexane. Yield 2.6 g (oil).

Workup

  1. temperaturethe mixture was refluxed for 2.5 h
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue obtained
  6. customwas purified by flash chromatography on silica-gel

Sources & evidence

ORD record
ord-14d1beaeaf0c40ba982328f6cde7761f
Source dataset
uspto-grants-1995_03
Patent number
US05401745

Reaction notes

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