Benzoyl Peroxide → Ethyl 2-(bromomethyl)benzoate

HRID 1195022Notes

Reaction equation

HRID 1195022 reaction equation
[C:1]1([CH3:12])[C:2]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=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][CH2:12][C:1]1[C:2]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 66598Ethyl 2-methylbenzoateHCID 67184N-bromobutanimide

Product 1

HCID 11032082Ethyl 2-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 100 g. of ethyl o-toluate, 100 g. of N-bromosuccinimide, and 0.3 g. of benzoyl peroxide in 1 liter of carbon tetrachloride is heated under reflux for 3 hours with stirring and filtered. The filtrate is washed with 3% aqueous sodium hydroxide and then with water, dried over magnesium sulfate, and concentrated under reduced pressure to provide ethyl α-bromo-o-toluate as an oil.

Workup

  1. additionA mixture of 100 g
  2. temperatureunder reflux for 3 hours
  3. filtrationfiltered
  4. washThe filtrate is washed with 3% aqueous sodium hydroxide
  5. dry with materialwith water, dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b71d28e499d34f10bb586add5fb8a08e
Source dataset
uspto-grants-1989_03
Patent number
US04816591

Reaction notes

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