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

HRID 1873394

反応式

HRID 1873394 の反応式
Br[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.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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 1370132-BromoselenopheneHCID 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 178418397HCID 178418397、化合物触媒HCID 21863594Toluene ethanol溶媒

実験手順

A mixture of 45.0 g (0.21 mol) of 2-bromoselenophene, 52.0 g (0.26 mol) of 4-ethoxy-2,3-difluorophenylboronic acid, 20.0 g (17.3 mmol) of tetrakis(triphenylphosphine)palladium(0) and 600 ml of 2 N sodium carbonate soln. in 1100 ml of toluene/ethanol (1:1) is heated under reflux for 20 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted with toluene. The combined organic phases are washed with sat. sodium hydrogencarbonate soln., 1 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:toluene=3:2). Further purification is carried out by recrystallisation from ethanol; 2-(4-ethoxy-2,3-difluorophenyl)selenophene is obtained as a beige solid.

後処理

  1. temperatureunder reflux for 20 h
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted with toluene
  5. washThe combined organic phases are washed with sat. sodium hydrogencarbonate soln
  6. customThe solution is dried
  7. concentrationconcentrated to dryness
  8. customThe residue is purified by column chromatography (SiO2, n-heptane:toluene=3:2)
  9. customFurther purification
  10. customis carried out by recrystallisation from ethanol

出典と根拠

ORDレコード
ord-b0d75b2282834822b4ffc49a3ff86c7a
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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