Tetrahydrofuran → 3,5-Difluoro-4'-propyl-1,1'-biphenyl

HRID 1406822노트

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HRID 1406822 반응식
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].C1COCC1.[F:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[C:27]([F:29])[CH:28]=1>CCCCCC>[F:22][C:23]1[CH:24]=[C:25]([C:7]2[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=2)[CH:26]=[C:27]([F:29])[CH:28]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 1363741-Bromo-4-propylbenzeneHCID 2734338(3,5-Difluorophenyl)boronic acid

생성물 1

HCID 156387533,5-Difluoro-4'-propyl-1,1'-biphenyl수율 99.6%

시약·촉매·용매 1

HCID 8058Hexane용매

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온도
60 °C

실험 절차

In a nitrogen atmosphere, a solution prepared by mixing 90.33 g of 4-propylbromobenzene, 2.62 g of tetrakis-triphenylphosphine palladium, 240 mL of an aqueous potassium carbonate solution (2 mol/L), and 450 mL of THF was heated to 60° C., and 71.65 g of 3,5-difluorophenylboronic acid was added to the solution over 30 minutes. The resultant mixture was stirred at 60° C. for 30 minutes and then allowed to cool. Then, hexane was added to the mixture to separate an organic layer, and the organic layer was washed with saturated brine and dried by adding sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to yield 104.92 g of 3,5-difluoro-1-(4-propylphenyl)benzene.

후처리

  1. customIn a nitrogen atmosphere, a solution prepared
  2. temperatureto cool
  3. customto separate an organic layer
  4. washthe organic layer was washed with saturated brine
  5. customdried
  6. additionby adding sodium sulfate
  7. distillationThen, the solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-836541e00bdb46cc860a99569269ab0e
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916718B2

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