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

HRID 1943513

반응식

HRID 1943513 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 21863594Toluene ethanol용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-05f7bf8fa6664e07a70360f0b33c850a
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394293B2

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