Benzene → HCID 54565929, compound

HRID 279470Notes

Reaction equation

HRID 279470 reaction equation
C1C=CC=CC=1.[CH3:7][O:8][N:9]=[C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[C:11]#[N:12].[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>CCCCCC>[Br:20][CH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10](=[N:9][O:8][CH3:7])[C:11]#[N:12]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 54206107HCID 54206107, compound

Product 1

HCID 54565929HCID 54565929, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Benzene (80 ml) was added to α-methoxyimino-2-methylphenylacetonitrile (isomer A)(4.0 g, 23 mmol) and N-bromosuccinimide (4.9 g, 28 mmol), and the mixture was heated under reflux for 1 hour in the presence of azobisiso-butyronitrile (190 mg, 1.2 mmol) as a radical initiator. After allowing the mixture to stand for cooling, n-hexane (100 ml) was added, and the mixture was allowed to stand overnight, and the resulting insoluble materials were filtered off. The filtrate was concentrated to dryness under reduced pressure and purified by column chromatography on silica gel (ethyl acetate/n-hexane) to give 2-bromomethyl-α-methoxyiminophenyl-acetonitrile (4.4 g, 76%) as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperaturefor cooling
  3. filtrationthe resulting insoluble materials were filtered off
  4. concentrationThe filtrate was concentrated to dryness under reduced pressure
  5. custompurified by column chromatography on silica gel (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-307da5aa62714170abc7b00916bcf428
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

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