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

HRID 1429359Notes

Reaction equation

HRID 1429359 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:19][CH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 33094Methyl o-toluateHCID 67184N-bromobutanimide

Product 1

HCID 2734813Methyl 2-(bromomethyl)benzoateYield 623.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of methyl 2-(methyl)benzoate 3a (9.46 g, 6.3 mmol) in chloroform (200 mL) were added NBS (13.8 g, 7.6 mmol) and benzoyl peroxide (760 mg, 0.32 mmol). The reaction mixture was stirred at reflux overnight. When the mixture was cooled to rt, filtered and concentrated. The residue was purified by CC, eluted with PE to give 3b as a colorless oil (9 g, 62% yield).

Workup

  1. temperatureat reflux overnight
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by CC
  5. washeluted with PE

Sources & evidence

ORD record
ord-b31d9be04694445ca9d1dab85ce63f40
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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