Benzoyl Peroxide → Methyl 5-bromo-2-(bromomethyl)benzoate

HRID 1442799Notes

Reaction equation

HRID 1442799 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[CH3:11].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[CH2:11][Br:13]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 316201Methyl 5-bromo-2-methylbenzoate

Product 1

HCID 12929136Methyl 5-bromo-2-(bromomethyl)benzoateYield 46%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 5-bromo-2-methylbenzoic acid methyl ester (8.4 g, 37 mmol) in 100 mL CCl4 was added N-bromosuccinimide (7.8 g, 44 mmol) and benzoylperoxide (0.5% as catalyst). The mixture was heated at reflux for 2 h and then was cooled to room temperature. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (petroleum ether) to afford 5-bromo-2-bromomethyl-benzoic acid methyl ester (5.2 g, 46%). 1H NMR (300 MHz, CDCl3) δ 8.09 (s, 1H), 7.60 (d, J=8.0, 1H), 7.32 (d, J=8.0, 1H), 4.89 (s, 2H), 3.94 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by column chromatography on silica gel (petroleum ether)

Sources & evidence

ORD record
ord-d6856e6a4b024d748622b0c52148e076
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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