Benzoyl Peroxide → Methyl 3-(bromomethyl)benzoate

HRID 226258

Reaction equation

HRID 226258 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 7435Benzoic acid, 3-methyl-, methyl esterHCID 67184N-bromobutanimide

Product 1

HCID 517981Methyl 3-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5.5 g (36 mmol) of methyl 3-methylbenzoate, 7.1 g (39.5 mmol) of N-Bromosuccinimide and 0.44 g (1.8 mmol) of benzoyl peroxide in 75 ml of Cl4C is refluxed for 5 h. The solid is filtered and washed with Cl4C. The mother liquors are concentrated and a yellow solid is obtained which is, essentially, monobromated product. This is used in the next step without further purification.

Workup

  1. temperatureis refluxed for 5 h
  2. filtrationThe solid is filtered
  3. washwashed with Cl4C
  4. concentrationThe mother liquors are concentrated
  5. customa yellow solid is obtained which
  6. customThis is used in the next step without further purification

Sources & evidence

ORD record
ord-be0a5fcfdd5242d0a7929c42ccb8756c
Source dataset
uspto-grants-2009_07
Patent number
US07557212B2

Linked notes

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