N-bromobutanimide → 1-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-

HRID 1018072ノート

反応式

HRID 1018072 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:15])[CH3:14])=[CH:9][CH:8]=1)=[O:6].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:16][C:13]([C:10]1[CH:9]=[CH:8][C:7]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])=[CH:12][CH:11]=1)([CH3:15])[CH3:14]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 987444-Chloro-4'-isopropylbutyrophenone

生成物 1

HCID 100635791-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-収率 100.9%

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
85 °C

実験手順

Dissolve 4-chloro-1-(4-isopropyl-phenyl)-butan-1-one (5.00 g, 22.2 mmol) and N-bromosuccinimide (4.1 g, 23.0 mmol) in carbon tetrachloride (25 mL) and add AIBN radical initiator (300 mg). Stir and maintain under a nitrogen atmosphere at 80-90° C. or optionally irradiate with a sunlamp until a vigorous exotherm occurs at which point momentarily remove until reflux subsides and then reapply the heat. Reflux for 30 minutes and add another potion of N-bromosuccinimide (100 mg) while maintaining reflux and reflux an additional 15 minutes. Cool to room temperature and precipitate the succinimide from the solution by allowing to stand overnight. Filter and wash the succinimide (2.25 g) with carbon tetrachloride (20 mL). Combine the filtrates and evaporate the solvent in vacuo to give the title compound as a yellow oil (6.80 g, 100%).

後処理

  1. customoptionally irradiate with a sunlamp until a vigorous exotherm
  2. custommomentarily remove
  3. temperatureuntil reflux subsides
  4. temperatureReflux for 30 minutes
  5. additionadd another potion of N-bromosuccinimide (100 mg)
  6. temperaturewhile maintaining
  7. temperaturereflux
  8. temperaturereflux an additional 15 minutes
  9. temperatureCool to room temperature
  10. customprecipitate the succinimide from the solution
  11. filtrationFilter
  12. washwash the succinimide (2.25 g) with carbon tetrachloride (20 mL)
  13. customCombine the filtrates and evaporate the solvent in vacuo

出典と根拠

ORDレコード
ord-995e3d6976de4b818da0a55f60a693e4
出典データセット
uspto-grants-2002_11
特許番号
US06479663B2

反応ノート

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