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

HRID 892131Notes

Reaction equation

HRID 892131 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.CCOCC>[Br:13][CH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

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

Product 1

HCID 10263795Methyl 2-(bromomethyl)-6-methylbenzoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl 2,6-dimethyl-benzoate (22.0 g, 134 mmol, example 1) in CCl4 (250 mL) is added N-bromo-succinimide (19 g, 107 mmol) followed by benzoyl peroxide (1.0 g, 4.0 p mmol). The resulting solution is warmed to reflux and stirred at this temperature for 20 min. The reaction mixture is then allowed to cool before being diluted with ether (200 mL), filtered and concentrated. The residue is purified by flash chromatography (silica, 4% acetone in hexanes) to give the title compound. This product (approx. 85% purity, remainder is methyl 2,6dimethyl benzoate) is used without further purification. MS (EI) 242, 244 (M+, Br pattern).

Workup

  1. temperatureThe resulting solution is warmed
  2. temperatureto reflux
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography (silica, 4% acetone in hexanes)

Sources & evidence

ORD record
ord-5306535214024b87bb992ad6105fe8e5
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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