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

HRID 590984

반응식

HRID 590984 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d74ffaa69872415e9aebab0a935931fd
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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