Bromine → Ethyl 5-bromo-6-(5-chloro-2-thienyl)-6-oxohexanoate

HRID 563103

反応式

HRID 563103 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:17])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.[Br:18]Br.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:18][CH:8]([C:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:17])[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

参加物

5

反応物 3

HCID 24408Bromine2 回HCID 24437Sodium SulfiteHCID 18174688Ethyl 6-(5-chloro-2-thienyl)-6-oxohexanoate

生成物 1

HCID 18174681Ethyl 5-bromo-6-(5-chloro-2-thienyl)-6-oxohexanoate収率 118.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Ethyl 6-(5-chloro-2-thienyl)-6-oxohexanoate (50.0 g) was dissolved in methylene chloride (150 ml), to which was added dropwise bromine (24.5 g) with stirring at room temperature. The mixture was stirred at room temperature for 1 hour, a 10% aqueous solution of sodium sulfite was then carefully added until disappearance of the red color of bromine, which was extracted with diethyl ether (200 ml×2). The organic layer was washed with a 10% aqueous solution of sodium hydrogen carbonate (100 ml), dried over anhydrous magnesium sulfate, and concentrated to give ethyl 5-bromo-6-(5-chloro-2-thienyl)-6-oxohexanoate as an oil (64.4 g, >99%).

後処理

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. extractionwas extracted with diethyl ether (200 ml×2)
  3. washThe organic layer was washed with a 10% aqueous solution of sodium hydrogen carbonate (100 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-6aaca899621744af96f3a2ab3e9050ca
出典データセット
uspto-grants-2011_11
特許番号
US08067453B2

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