Benzoyl Peroxide → Methyl 2-(bromomethyl)benzoate

HRID 1189321Notes

Reaction equation

HRID 1189321 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10].C1C(=O)N([Br:19])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][Br:19]

Participants

4

Reactant 3

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

Product 1

HCID 2734813Methyl 2-(bromomethyl)benzoateYield 92.2%

Procedure

A solution of methyl-2-methylbenzoate (250 mg, 1.66 mmol), NBS (296 mg, 1.66 mmol) and dibenzoylperoxide (403 mg, 1.66 mmol) was stirred under reflux for one day. After purification by flash chromatography, 350 mg (1.53 mmol, 92%) of methyl-2-(bromomethyl)benzoate were obtained as a colorless oil.

Workup

  1. temperatureunder reflux for one day
  2. customAfter purification by flash chromatography

Sources & evidence

ORD record
ord-8b0fc553824a4f1199f88cde4c16180f
Source dataset
uspto-grants-2014_03
Patent number
US08674106B2

Reaction notes

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