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

HRID 274927Notes

Reaction equation

HRID 274927 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]1[O:17][C:16]2[CH:15]=[CH:14][C:13]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:12][C:11]=2[O:10]1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH:18]([C:13]1[CH:14]=[CH:15][C:16]2[O:17][CH2:9][O:10][C:11]=2[CH:12]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (3.95 g, 22.2 mmol) and AlBN (0.098 g, 0.06 mMol) were added to a solution of methyl (3,4-methylenedioxyphenyl)acetate (3.9 g, 21.2 mmol) in carbon tetrachloride and the mixture was refluxed for 2.5 h. The reaction was cooled and filtered. The flitrate 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 flitrate was concentrated in vacuo
  5. customthe residue obtained
  6. customwas purified by flash chromatography on silica-gel

Sources & evidence

ORD record
ord-a9cf8f7d1d0a4ed0a7d2735fe2105d2e
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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