Benzoyl Peroxide → Methyl 4-(bromomethyl)-2-methoxybenzoate

HRID 874817Notes

Reaction equation

HRID 874817 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:32]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:32][CH2:13][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([O:2][CH3:1])[CH:12]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 7172021Methyl 2-methoxy-4-methylbenzoate

Product 1

HCID 11288398Methyl 4-(bromomethyl)-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl 2-methoxy-4-methylbenzoate (2.07 g, 11.5 mmol) in chloroform (30 mL) was added benzoyl peroxide (0.14 g, 0.57 mmol) and N-bromosuccinimide (2.04 g, 11.5 mmol). The reaction mixture was heated at reflux for 3 hours. The reaction mixture was washed with saturated sodium hydrogen carbonate and the organic phase was poured through a hydrophobic frit and the solvent evaporated at reduced pressure. The crude material was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. washThe reaction mixture was washed with saturated sodium hydrogen carbonate
  4. additionthe organic phase was poured through a hydrophobic frit
  5. customthe solvent evaporated at reduced pressure
  6. customThe crude material was used in the next step without further purification

Sources & evidence

ORD record
ord-0645c163ccfc4b3da830f1c3480f61da
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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