N-bromobutanimide → (E)-Methyl 2-(methoxyimino)-2-[2-(bromomethyl)phenyl]acetate

HRID 1491981Notes

Reaction equation

HRID 1491981 reaction equation
[CH3:1][O:2][C:3](=[O:15])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])=[N:5]/[O:6][CH3:7].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][Br:16])=[N:5]/[O:6][CH3:7]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 10998216Methyl (2E)-(methoxyimino)(2-methylphenyl)acetate

Product 1

HCID 10989774(E)-Methyl 2-(methoxyimino)-2-[2-(bromomethyl)phenyl]acetateYield 106.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl-(E)-2-(2-tolyl)-2-methoxyiminoacetate (4.74 g) was dissolved in carbon tetrachloride (100 ml), and N-bromosuccinimide (4.89 g) and benzoylperoxide (554 mg) were added thereto. The resultant mixture was heated under reflux for 1 hour and cooled to room temperature. Insoluble materials were removed by filtration. On concentration of the solvent, the residue was purified by silica gel column chromatography with a mixture of hexane and ethyl acetate to give methyl-(E)-2-(2-bromomethylphenyl)-2-methoxyiminoacetate (6.98 g).

Workup

  1. temperatureunder reflux for 1 hour
  2. customInsoluble materials were removed by filtration
  3. customOn concentration of the solvent, the residue was purified by silica gel column chromatography with a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-b7e5a53db21f46db8890ab0fa1214e58
Source dataset
uspto-grants-1994_12
Patent number
US05371222

Reaction notes

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