Benzoyl Peroxide → HCID 19429904, compound

HRID 2081636Notes

Reaction equation

HRID 2081636 reaction equation
[CH3:1][O:2][C:3](=[O:22])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=1)=[N:5]/[O:6][CH3:7].[Br:23]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:22])/[C:4](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][Br:23])[CH:16]=1)=[N:5]/[O:6][CH3:7]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 11748553HCID 11748553, compound

Product 1

HCID 19429904HCID 19429904, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (E)-methyl-2-[2-(3-methylphenoxy)phenyl]-2-methoxyiminoacetate (4.60 g) in benzene (120 ml), N-bromosuccinimide (2.88 g) and benzoyl peroxide (0.37 g) were added, and the resultant mixture was refluxed for 1 hour, followed by cooling to room temperature. Insoluble materials were removed by filtration and, after removal of the solvent, the residue was purified by silica gel column chromatography to give (E)-methyl-2-[2-(3-bromomethylphenoxy)phenyl]-2-methoxyiminoacetate (4.60 g).

Workup

  1. customInsoluble materials were removed by filtration
  2. customafter removal of the solvent
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ac9e5d75e7324cc787019f3e81407c3c
Source dataset
uspto-grants-1993_02
Patent number
US05185342

Reaction notes

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