N-bromobutanimide → HCID 86619641, compound

HRID 1774399Notes

Reaction equation

HRID 1774399 reaction equation
[CH3:1]/[C:2](=[C:7](\[CH3:12])/[C:8]([O:10][CH3:11])=[O:9])/[C:3]([O:5][CH3:6])=[O:4].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:13][CH2:12]/[C:7](=[C:2](\[CH3:1])/[C:3]([O:5][CH3:6])=[O:4])/[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 10953983HCID 10953983, compound

Product 1

HCID 86619641HCID 86619641, compoundYield 26.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of dimethyl 2,3-dimethylmaleate (500 mg, 2.90 mmol) in carbon tetrachloride (11 mL) were added N-bromosuccinimide (803 mg, 4.51 mmol) and 2,2′-azobisisobutyronitrile (3.2 mg, 0.019 mmol) at room temperature, and the mixture was heated under reflux with stirring for 4 h. The reaction mixture was directly filtrated, and the filtrate was washed with water and brine. The residue obtained by concentrating the organic layer under reduced pressure was subjected to silica gel column chromatography (hexane-ethyl acetate 20:1→8:1) to give 191 mg of dimethyl 2-bromomethyl-3-methylmaleate (yield: 26%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. filtrationThe reaction mixture was directly filtrated
  4. washthe filtrate was washed with water and brine
  5. customThe residue obtained
  6. concentrationby concentrating the organic layer under reduced pressure

Sources & evidence

ORD record
ord-53419ba7058c4b22ba1d15666965fd1a
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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