Benzoyl Peroxide → Methyl 3-bromo-4-(bromomethyl)benzoate

HRID 735856Notes

Reaction equation

HRID 735856 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([Br:11])[CH:5]=1.C1C(=O)N([Br:20])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:11][C:6]1[CH:5]=[C:4]([C:3]([O:2][CH3:1])=[O:12])[CH:9]=[CH:8][C:7]=1[CH2:10][Br:20]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 7015747Methyl 3-bromo-4-methylbenzoate

Product 1

HCID 10804694Methyl 3-bromo-4-(bromomethyl)benzoateYield 95.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl-3-bromo-4-methylbenzoate (40 g, 0.17 mol), NBS (34 g, 0.19 mol) and benzoylperoxide (4.0 g) in CCl4 (500 mL) was refluxed for 6 h. The reaction mixture was cooled and filtered off the solid. The filtrate was concentrated under vacuum to give 2-bromo-4-methoxycarbonylbenzyl bromide (50 g, 93%) as a solid.

Workup

  1. temperaturewas refluxed for 6 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered off the solid
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-a9d8b506e1e94502b94a85888fae1621
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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