Methyl o-toluate → Methyl 2-(bromomethyl)benzoate

HRID 1242082Notes

Reaction equation

HRID 1242082 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].[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[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:12]

Participants

5

Reactant 2

HCID 33094Methyl o-toluateHCID 67184N-bromobutanimide

Product 1

HCID 2734813Methyl 2-(bromomethyl)benzoateYield 89.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 6212ChloroformSolvent

Procedure

2-Methyl-benzoic acid methyl ester (1.50 g 10 mmol), N-bromosuccinimide (1.96 g, 11 mmol) and 2,2′-azobis(2-methylpropionitrile) (AIBN) (25 mg, 0.15 mmol) were dissolved in chloroform (3 ml). The solution was heated at reflux for 16 h. cooled and the solvent evaporated in vacuo. The residue was purified by silica gel chromatography using a gradient of ethyl acetate/hexane (1–2%) as eluant. Pure fractions were collected and the solvent evaporated in vacuo affording 2.05 g (89%) of 2-bromomethyl-benzoic acid methyl ester as a solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 16 h.
  3. temperaturecooled
  4. customthe solvent evaporated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. customPure fractions were collected
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-1b4fa76a0c094057bc1b4b7f8b0c4187
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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