Potassium Carbonate → 3',4',5'-Trifluoro-[1,1'-biphenyl]-4-carbaldehyde

HRID 1406828

반응식

HRID 1406828 반응식
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].[CH:17]([C:19]1[CH:24]=[CH:23][C:22](OB(O)O)=[CH:21][CH:20]=1)=[O:18]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:22]2[CH:23]=[CH:24][C:19]([CH:17]=[O:18])=[CH:20][CH:21]=2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 6114091-Bromo-3,4,5-trifluorobenzeneHCID 21940015p-Formylphenylboric acid

생성물 1

HCID 612398773',4',5'-Trifluoro-[1,1'-biphenyl]-4-carbaldehyde수율 96.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

In a nitrogen atmosphere, a solution prepared by mixing 15.00 g of 3,4,5-trifluorobromobenzene, 0.25 g of tetrakis-triphenylphosphine palladium, 30 mL of an aqueous potassium carbonate solution (2 mol/L), and 75 mL of THF was heated to 60° C., and 10.71 g of 4-formylphenylboric acid was added to the solution over 20 minutes. After the resultant mixture was stirred at 60° C. for 3 hours, the mixture was allowed to cool, and an organic layer was separated by adding hexane. The organic layer was washed with saturated brine and dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure. As a result of purification by silica gel column chromatography, 14.77 g of 4-(3,4,5-trifluorophenyl)benzaldehyde was yielded.

후처리

  1. customIn a nitrogen atmosphere, a solution prepared
  2. temperatureto cool
  3. customan organic layer was separated
  4. additionby adding hexane
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. additionby adding sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customAs a result of purification by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1f4bff464cbe48f4820367ccdde28900
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916718B2

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