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

HRID 334066ノート

反応式

HRID 334066 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-dc6b77f0f1f9494da3b4fa7efd91737a
出典データセット
uspto-grants-2014_11
特許番号
US08883789B2

反応ノート

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