Benzoyl Peroxide → Methyl 2-Bromo-2-phenoxyacetate

HRID 2253570Notes

Reaction equation

HRID 2253570 reaction equation
[O:1]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:13][CH:8]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 16365Methyl phenoxyacetateHCID 67184N-bromobutanimide

Product 1

HCID 13063397Methyl 2-Bromo-2-phenoxyacetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl phenoxyacetate (5.0 g, 30 mmol), N-bromosuccinimide (5.4 g, 30 mmol), a few crystals (0.2 to 0.5 g) of benzoyl peroxide, and 50 mL of carbon tetrachloride were placed in a 100 ml flask and heated at reflux with stirring for about 4 hr. The mixture was then allowed to cool, was filtered, and was concentrated by evaporation under reduced pressure to obtain 6.6 g (90 percent of theory) of the title compound as a red oil.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureto cool
  4. filtrationwas filtered
  5. concentrationwas concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-b5140f8e3fe74cd8ae2a5968261836b9
Source dataset
uspto-grants-1993_08
Patent number
US05232896

Reaction notes

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