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Methyl acetoacetate → 5-Bromo-2-methyl-benzofuran-3-carboxylic acid methyl ester

HRID 334066
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HRID 334066 반응식
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=1I.[C:16]([O:22][CH3:23])(=[O:21])[CH2:17][C:18]([CH3:20])=[O:19]>C1COCC1.CCOC(C)=O.[Cu]I>[CH3:23][O:22][C:16]([C:17]1[C:9]2[CH:10]=[C:11]([Br:14])[CH:12]=[CH:13][C:8]=2[O:19][C:18]=1[CH3:20])=[O:21]
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참가 물질

7

반응물 3

HCID 7757Methyl acetoacetateHCID 11430Potassium CarbonateHCID 134063481,4-Dibromo-2-iodobenzene

생성물 1

HCID 866882895-Bromo-2-methyl-benzofuran-3-carboxylic acid methyl ester

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 8028
Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a stirred mixture of 100 mg (0.525 mmol) copper(I)iodide and 1.90 g (13.7 mmol) potassium carbonate in 10 mL THF was added 1.75 g (4.84 mmol) 1,4-dibromo-2-iodo-benzene and 520 μL methyl acetoacetate under argon atmosphere. Then the mixture was stirred at 100° C. for 5 h under reflux. The reaction mixture was diluted with EtOAc and extracted with water. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (PE/EtOAc=9/1).

후처리

  1. temperatureunder reflux
  2. extractionextracted with water
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (PE/EtOAc=9/1)

출처 및 근거

ORD 기록
ord-dc6b77f0f1f9494da3b4fa7efd91737a
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08883789B2

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