Sodium Carbonate → 2-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-methylthiophene

HRID 1943513

反応式

HRID 1943513 の反応式
Br[C:2]1[S:3][C:4]([CH3:7])=[CH:5][CH:6]=1.[CH2:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19](B(O)O)=[C:18]([F:25])[CH:17]=2)=[CH:12][CH:11]=1)[CH3:9].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>[CH2:8]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:2]3[S:3][C:4]([CH3:7])=[CH:5][CH:6]=3)=[C:18]([F:25])[CH:17]=2)=[CH:14][CH:15]=1)[CH3:9]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 698312-Bromo-5-methylthiopheneHCID 534025754'-Ethyl-3-fluorobiphenyl-4-boronic acid

生成物 1

HCID 581606952-(4'-Ethyl-3-fluorobiphenyl-4-yl)-5-methylthiophene

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 5.0 g (28.2 mmol) of 2-bromo-5-methylthiophene, 7.70 g (28.3 mmol) of 4′-ethyl-3-fluoro-4-biphenylboronic acid, 1.70 g (1.47 mmol) of tetrakis(triphenylphosphine)palladium(0) and 30 ml of 2 N sodium carbonate solution in 90 ml of toluene/ethanol (1:2) is refluxed for 3 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted a number of times with toluene. The combined organic phases are washed with water and sat. sodium chloride solution. The solution is dried using sodium sulfate and evaporated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:toluene=97:3). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 2-(4′-ethyl-3-fluorobiphenyl-4-yl)-5-methylthiophene as a colourless solid (m.p. 102° C.).

後処理

  1. temperatureis refluxed for 3 h
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted a number of times with toluene
  5. washThe combined organic phases are washed with water and sat. sodium chloride solution
  6. customThe solution is dried
  7. customevaporated to dryness
  8. customThe residue is purified by column chromatography (SiO2, n-heptane:toluene=97:3)
  9. customThe further purification
  10. customis carried out by recrystallisation from ethanol and n-heptane

出典と根拠

ORDレコード
ord-05f7bf8fa6664e07a70360f0b33c850a
出典データセット
uspto-grants-2013_03
特許番号
US08394293B2

関連ノート

読み込み中…