Sodium Carbonate → HCID 58028452, 화합물

HRID 449732

반응식

HRID 449732 반응식
Br[C:2]1[S:3][C:4]([CH3:7])=[CH:5][CH:6]=1.[CH2:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[C:21]([F:23])[C:20](B(O)O)=[C:19]([F:27])[CH:18]=2)=[CH:13][CH:12]=1)[CH2:9][CH3:10].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>[F:23][C:21]1[CH:22]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([CH2:8][CH2:9][CH3:10])=[CH:12][CH:13]=2)[CH:18]=[C:19]([F:27])[C:20]=1[C:2]1[S:3][C:4]([CH3:7])=[CH:5][CH:6]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 698312-Bromo-5-methylthiopheneHCID 58028431HCID 58028431, 화합물

생성물 1

HCID 58028452HCID 58028452, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 21863594Toluene ethanol용매

실험 절차

A mixture of 5.50 g (31.0 mmol) of 2-bromo-5-methylthiophene, 9.0 g (32.6 mmol) of 4′-propyl-3,5-difluoro-4-biphenylboronic acid, 1.83 g (1.58 mmol) of tetrakis(triphenylphosphine)palladium(0) and 36 ml of 2 N sodium carbonate soln. in 90 ml of toluene/ethanol (1:2) is heated under reflux for 16 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 soln. The solution is dried using sodium sulfate and concentrated to completion. The residue is purified by column chromatography (SiO2, n-heptane:toluene=9:1). Further purification is carried out by recrystallisation from ethanol and n-heptane; 2-(3,5-difluoro-4′-propylbiphenyl-4-yl)-5-methylthiophene (PUS-3-1) is obtained as a colourless solid (m.p. 75° C.).

후처리

  1. temperatureunder reflux for 16 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 soln
  6. customThe solution is dried
  7. concentrationconcentrated to completion
  8. customThe residue is purified by column chromatography (SiO2, n-heptane:toluene=9:1)
  9. customFurther purification
  10. customis carried out by recrystallisation from ethanol and n-heptane

출처 및 근거

ORD 기록
ord-8d5c3e19b21040d981c448917de5348d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486297B2

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