Carbon Tetrachloride → 3-(1-bromoethyl)-7-fluoroquinoxalin-2(1H)-one

HRID 1019820

反応式

HRID 1019820 の反応式
[CH2:1]([C:3]1[C:4](=[O:14])[NH:5][C:6]2[C:11]([N:12]=1)=[CH:10][CH:9]=[C:8]([F:13])[CH:7]=2)[CH3:2].[Br:15]N1C(C)(C)C(=O)N(Br)C1=O.C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>>[Br:15][CH:1]([C:3]1[C:4](=[O:14])[NH:5][C:6]2[C:11]([N:12]=1)=[CH:10][CH:9]=[C:8]([F:13])[CH:7]=2)[CH3:2]

参加物

6

反応物 5

HCID 5943Carbon TetrachlorideHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 7187Benzoyl PeroxideHCID 516892Sodium BicarbonateHCID 672892053-ethyl-7-fluoroquinoxalin-2(1H)-one

生成物 1

HCID 866985193-(1-bromoethyl)-7-fluoroquinoxalin-2(1H)-one収率 133%

反応条件

温度
80 °C

実験手順

3-Ethyl-7-fluoroquinoxalin-2(1H)-one (20.61 g, 107.2 mmol) and 1,3-dibromo-5,5-dimethylhydantoin (18.77 g, 64.34 mmol) suspended in carbon tetrachloride (1072 ml, 107.2 mmol). To the heterogeneous mixture was added benzoyl peroxide (3.463 g, 10.72 mmol) and the mixture was heated at reflux with stirring (oil bath temperature: 80° C.) for 20 h. After 20 h, the mixture was cooled to rt. After cooling, the mixture was poured into saturated aqueous sodium bicarbonate solution (1 L) with stirring. The precipitate was collected by filtration and washed with water (1 L) to give 3-(1-bromoethyl)-7-fluoroquinoxalin-2(1H)-one (23.19 g, 79.8% yield) as a tan solid:

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. waitAfter 20 h
  4. temperaturethe mixture was cooled to rt
  5. temperatureAfter cooling
  6. stirringwith stirring
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with water (1 L)

出典と根拠

ORDレコード
ord-ae08bcbc30f44f089ad7b8d076fba8d7
出典データセット
uspto-grants-2014_05
特許番号
US08716290B2

関連ノート

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