Benzoyl Peroxide → Propanedioic acid, (2-bromo-1-methylethylidene)-, diethyl ester

HRID 746472Notes

Reaction equation

HRID 746472 reaction equation
[C:1](=[C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])([CH3:3])[CH3:2].[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:3][C:1](=[C:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 81255Diethyl isopropylidenemalonate

Product 1

HCID 11254458Propanedioic acid, (2-bromo-1-methylethylidene)-, diethyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

Diethyl isopropylidenemalonate (4, 50 g, 0.25 mol) was refluxed with stirring with N-bromosuccinimide (44.3 g, 0.25 mol) and dibenzoyl peroxide (1.0 g, 4.1 mmol) in carbon tetrachloride (100 mL) with illumination using Kodak Ectagraphic slide projector lamp ELH (300 Watt) for 1.5 h. The reaction was completed as indicated by a negative starch-iodine test for N-bromosuccinimide. The resulting mixture was diluted with carbon tetrachloride (100 mL) and it was cooled in an ice-bath. The precipitated succinimide was filtered off and the filtrate was evaporated in vacuo at room temperature. The residual pale yellow oil of diethyl bromo-isopropylidene-malonate (5, 71.1 g) was used without purification in the Example 2.

Workup

  1. customfor 1.5 h
  2. temperaturewas cooled in an ice-bath
  3. filtrationThe precipitated succinimide was filtered off
  4. customthe filtrate was evaporated in vacuo at room temperature
  5. customThe residual pale yellow oil of diethyl bromo-isopropylidene-malonate (5, 71.1 g) was used without purification in the Example 2

Sources & evidence

ORD record
ord-0c382508cafd40f4a9f57d3c7fc7a0e6
Source dataset
uspto-grants-2008_07
Patent number
US07393855B2

Reaction notes

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