N-bromobutanimide → HCID 67548259, compound

HRID 2233168Notes

Reaction equation

HRID 2233168 reaction equation
[F:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([N:6]=[CH:7][C:8]([O:13][CH3:14])=[N:9]2)=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:12][C:11]1[C:2]([F:1])=[CH:3][CH:4]=[C:5]2[C:10]=1[N:9]=[C:8]([O:13][CH3:14])[CH:7]=[N:6]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 675481507-Fluoro-2-methoxy-8-methylquinoxaline

Product 1

HCID 67548259HCID 67548259, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 6212ChloroformSolvent

Procedure

To 7-fluoro-8-methyl-2-(methyloxy)quinoxaline (50 g, 260 mmol) in dry chloroform (1 L) were added N-bromosuccinimide (52 g, 292 mmol) and benzoyl peroxide (70%, 0.42 g) and the mixture was heated under reflux, illuminated with a 120 W lamp, for 2 h. After cooling, the mixture was washed with water. The aqueous phase was re-extracted twice with dichloromethane and the combined organic fractions were washed with water, dried and evaporated to give product (72.1 g, 100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customilluminated with a 120 W lamp, for 2 h
  4. temperatureAfter cooling
  5. washthe mixture was washed with water
  6. extractionThe aqueous phase was re-extracted twice with dichloromethane
  7. washthe combined organic fractions were washed with water
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-a668946fd8ba448a9e187b8c7344b1b6
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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