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Water → 4-(2-Bromoethyl)-3-chloro-1,3-dihydro-2H-indol-2-one

HRID 358821
ノート
印刷プレビュー

反応式

HRID 358821 の反応式
C([Cl:4])(=O)C.[Br:5][CH2:6][CH2:7][C:8]1[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=1[CH:10]=[CH:11][N+:12]([O-])=O.[OH2:19]>ClCCl>[Br:5][CH2:6][CH2:7][C:8]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:9]=1[CH:10]([Cl:4])[C:11](=[O:19])[NH:12]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962Water2 回HCID 6367Acetyl chlorideHCID 534279492-(2'-Bromoethyl)-beta-nitrostyrene

生成物 1

HCID 103560034-(2-Bromoethyl)-3-chloro-1,3-dihydro-2H-indol-2-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
20 °C

実験手順

To a precooled solution of ferric chloride (28.5 kg) in dichloromethane (340 1) at 0° C. was added acetyl chloride (9.2 kg) at such a rate that the reaction temperature did not exceed 5° C. The reaction mixture was stirred at between 0° and 5° C. for 15 minutes. To the mixture was added a pre-dryed solution of 2-(2'-bromoethyl)-β-nitrostyrene [12.88 kg (16.22 kg wet:water content 20.6%)]in dichloromethane (55 litres) at such a rate that the reaction temperature did not exceed 5° C. The reaction mixture was stirred for 5 hours at a temperature between 5 and 10° C. Analysis by TLC confirmed that the reaction had gone to completion. Water (240 1) was then added to the reaction mixture at such a rate so that the temperature did not exceed 20° C. The mixture was then stirred for 30 minutes. The dichloromethane layer was isolated and washed a further three times with water (three times 120 1). The dichloromethane layer was then distilled to a volume of about 60 1. After cooling to 20° C. petroleum ether (60/80 grade. 40 1) was added and the resulting precipitate was stirred at 10° C. for 30 minutes. HPLC analysis of the crude reaction mixture indicated a purity of 93.22% of the required product. 4-(2'-bromo-ethyl)-3-chloro-1,3-dihydro-2H-indol-2-on by filtration, the filtrate washed with petroleum ether (60 1) and dried at 80° C. overnight to give 10.8 kg (78%) of of the title compound.

後処理

  1. customdid not exceed 5° C
  2. customdid not exceed 5° C
  3. stirringThe reaction mixture was stirred for 5 hours at a temperature between 5 and 10° C
  4. customdid not exceed 20° C
  5. stirringThe mixture was then stirred for 30 minutes
  6. washwashed a further three times with water (three times 120 1)
  7. distillationThe dichloromethane layer was then distilled to a volume of about 60 1
  8. additionwas added
  9. stirringthe resulting precipitate was stirred at 10° C. for 30 minutes
  10. customHPLC analysis of the crude reaction mixture

出典と根拠

ORDレコード
ord-619c51b4cca1402991d7d75c08d4ab4d
出典データセット
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04997954

反応ノート

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