Benzoyl Peroxide → Methyl 2-(bromomethyl)benzoate

HRID 1070467Notes

Reaction equation

HRID 1070467 reaction equation
[C:1]1([CH3:11])[C:2]([C:7]([O:9][CH3:10])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[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[C:2]([C:7]([O:9][CH3:10])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 33094Methyl o-toluateHCID 67184N-bromobutanimide

Product 1

HCID 2734813Methyl 2-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl o-toluate (15.0 g, 0.1 mol) in carbon tetrachloride (200 ml) were added N-bromosuccinimide (18.7 g, 0.1 mol) and benzoyl peroxide (catalytic amount) and the mixture was refluxed under heating for 2 hr. The reaction mixture was cooled to room temperature and the resulting precipitate was filtered off. The filtrate was concentrated under reduced pressure to give methyl α-bromo-o-toluate (yellow oil). The obtained oil was used in the next reaction without purification.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hr
  3. filtrationthe resulting precipitate was filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6152b8b45f8a456fa1481f8291ac6e9b
Source dataset
uspto-grants-2005_06
Patent number
US06903094B2

Reaction notes

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