Benzoyl Peroxide → Methyl 2-(bromomethyl)-6-methylbenzoate

HRID 453862Notes

Reaction equation

HRID 453862 reaction equation
C1C(=O)N([Br:8])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[CH3:27][C:28]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:29]=1[C:30]([O:32][CH3:33])=[O:31]>>[Br:8][CH2:27][C:28]1[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[C:29]=1[C:30]([O:32][CH3:33])=[O:31]

Participants

4

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 519028Methyl 2,6-dimethylbenzoate

Product 1

HCID 10263795Methyl 2-(bromomethyl)-6-methylbenzoateYield 32%

Procedure

NBS (40.85 mmol, 1 equiv.) and benzoyl peroxide (10.21 mmol, 0.25 equiv.) were added to a solution of methyl 2,6-dimethylbenzoate (40 mmol, 1 equiv.) in CCL4 (75 ml), and the mixture was heated for 20 min at boiling temperature. The reaction mixture was filtered out over celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (1.5% ethyl acetate/hexane). Yield: 32%

Workup

  1. temperaturethe mixture was heated for 20 min
  2. filtrationThe reaction mixture was filtered out over celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography (1.5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-792b9c8f5b474dae80915b0548738485
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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