Benzoyl Peroxide → Methyl 2-(bromomethyl)benzoate

HRID 422504Notes

Reaction equation

HRID 422504 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-d631deca23a344b7baee6a9665977bb5
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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