Benzoyl Peroxide → [2-(Bromomethyl)phenyl]acetic acid

HRID 2185672Notes

Reaction equation

HRID 2185672 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([OH:10])=[O:9].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 69519o-Tolylacetic acid

Product 1

HCID 12889260[2-(Bromomethyl)phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

o-Tolylacetic acid (40 g, 266 mmol), N-bromosuccinimide (52.147 g, 293 mmol) and benzoyl peroxide (0.174 g, catalytic) are dissolved in 300 ml of CCl4. The suspension is brought to and maintained at reflux for 12 hours. After cooling, the solid particles are separated out by filtration. and the CCl4 is evaporated off under vacuum, which allows a white solid to appear. This is sufficiently pure without recrystallization.

Workup

  1. temperaturemaintained
  2. temperatureat reflux for 12 hours
  3. temperatureAfter cooling
  4. customthe solid particles are separated out by filtration
  5. customand the CCl4 is evaporated off under vacuum, which
  6. customThis is sufficiently pure without recrystallization

Sources & evidence

ORD record
ord-c4753d9f8431448fb020bf1229465105
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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