Benzoyl Peroxide → Methyl 3-bromo-2-(bromomethyl)benzoate

HRID 1712949Notes

Reaction equation

HRID 1712949 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:38])C(=O)C1>C1C=CC=CC=1>[Br:1][C:2]1[C:3]([CH2:12][Br:38])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 12929135Methyl 3-Bromo-2-methylbenzoate

Product 1

HCID 21907554Methyl 3-bromo-2-(bromomethyl)benzoateYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of methyl 3-bromo-2-methylbenzoate (26.6 mmol), benzoyl peroxide (2.7 mmol) and NBS (32 mmol) in benzene (80 mL) was allowed to stir at reflux for 5 hr. The reaction mixture was filtered and the solid was washed with diethyl ether. The organic solutions were combined and washed with 10% Na2S2O3 and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give methyl 3-bromo-2-(bromomethyl)benzoate (26.6 mmol, 100%) as an oil.

Workup

  1. temperatureat reflux for 5 hr
  2. filtrationThe reaction mixture was filtered
  3. washthe solid was washed with diethyl ether
  4. washwashed with 10% Na2S2O3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-34418ecd75324be484338c17051b6ea3
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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