Sodium Carbonate → 2-(4-Ethoxy-2,3-difluorophenyl)selenophene

HRID 1873393

反応式

HRID 1873393 の反応式
I[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[C:12]([F:19])[C:11]=1[F:20])[CH3:8].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CC(OC)(C)C>[CH2:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[Se:3][CH:4]=[CH:5][CH:6]=2)=[C:12]([F:19])[C:11]=1[F:20])[CH3:8]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 1421832-IodoselenopheneHCID 15135235B-(4-Ethoxy-2,3-difluorophenyl)boronic acid

生成物 1

HCID 594563012-(4-Ethoxy-2,3-difluorophenyl)selenophene

試薬・触媒・溶媒 2

HCID 15413tert-Butyl methyl ether溶媒HCID 21863594Toluene ethanol溶媒

実験手順

A mixture of 34.8 g (0.14 mol) of 2-iodoselenophene, 32.8 g (0.16 mol) of 4-ethoxy-2,3-difluorophenylboronic acid, 8.10 g (77.01 mmol) of tetrakis -(triphenylphosphine)palladium(0) and 300 ml of 2 N sodium carbonate soln. in 800 ml of toluene/ethanol (1:1) is heated under reflux for 23 h. The mixture is diluted with MTBE and washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with 2 N hydrochloric acid and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:EtOAc=15:1-10:1→5:1). Further purification is carried out by recrystallisation from n-heptane; 2-(4-ethoxy-2,3-difluorophenyl)selenophene is obtained as a beige solid.

後処理

  1. temperatureunder reflux for 23 h
  2. washwashed with water
  3. extractionThe aqueous phase is extracted with MTBE
  4. washthe combined organic phases are washed with 2 N hydrochloric acid and sat. sodium chloride soln
  5. customThe solution is dried
  6. concentrationconcentrated to dryness
  7. customThe residue is purified by column chromatography (SiO2, n-heptane:EtOAc=15:1-10:1→5:1)
  8. customFurther purification
  9. customis carried out by recrystallisation from n-heptane

出典と根拠

ORDレコード
ord-0762230a08e74588a5910f25485ffb77
出典データセット
uspto-grants-2012_11
特許番号
US08304036B2

関連ノート

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