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

HRID 75384

反応式

HRID 75384 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-92849659d0874c5281220a124d720487
出典データセット
uspto-grants-2014_09
特許番号
US08835432B2

関連ノート

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