Ethoxalyl chloride → Ethyl 3,5-dibromo-alpha-oxo-2-thiopheneacetate

HRID 590984

反応式

HRID 590984 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[S:7][CH:8]=[C:9]([Br:11])[CH:10]=1.Cl[C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>ClCCl>[Br:11][C:9]1[CH:10]=[C:6]([Br:5])[S:7][C:8]=1[C:13](=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

参加物

5

反応物 3

HCID 20884Ethoxalyl chlorideHCID 2724560Thiophene, 2,4-dibromo-HCID 6451240Aluminum(III) Chloride

生成物 1

HCID 14113379Ethyl 3,5-dibromo-alpha-oxo-2-thiopheneacetate収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Aluminium chloride (0.26 g, 1.98 mmol) was added to a solution of 2,4-dibromothiophene (0.30 g, 1.24 mmol) and ethyl chlorooxoacetate (0.19 g, 1.36 mmol) in dichloromethane (10 mL) previously cooled with an ice bath. The reaction mixture was stirred at room temperature 45 minutes, poured into ice water and extracted with dichloromethane (2×20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to provide the desired keto-ester (10a) (0.42 g, 1.24 mmol, 100%) as a yellow oil.

後処理

  1. temperaturepreviously cooled with an ice bath
  2. extractionextracted with dichloromethane (2×20 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d74ffaa69872415e9aebab0a935931fd
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

関連ノート

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