N-bromobutanimide → Methyl 5-(bromomethyl)-2-methoxybenzoate

HRID 1531917

Reaction equation

HRID 1531917 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[O:11][CH3:12].[Br:14]N1C(=O)CCC1=O>C1C=CC=CC=1>[Br:14][CH2:10][C:8]1[CH:7]=[CH:6][C:5]([O:11][CH3:12])=[C:4]([CH:9]=1)[C:3]([O:2][CH3:1])=[O:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 10241396Methyl 2-methoxy-5-methylbenzoate

Product 1

HCID 19744340Methyl 5-(bromomethyl)-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-methoxy-5-methylbenzoic acid methyl ester (J.Chem.Soc.Perkin Trans.1, 1994, 1125) (1.47 g) and N-bromosuccinimide (1.45 g) in benzene (15 ml) was irradiated under a 500 W halogen lamp for 3 hours. The solvent was evaporated and the residue triturated with diethyl ether. The succinimide was filtered off and the filtrate evaporated.

Workup

  1. customThe solvent was evaporated
  2. customthe residue triturated with diethyl ether
  3. filtrationThe succinimide was filtered off
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-cc5a220a1f5644198b9e4917cab8fd4f
Source dataset
uspto-grants-2001_03
Patent number
US06200981B1

Linked notes

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