4-Iodophenol → 2',4'-Difluoro(1,1'-biphenyl)-4-ol

HRID 547843노트

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HRID 547843 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1B(O)O.I[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1

참가 물질

7

반응물 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 27343342,4-Difluorophenylboronic acid

생성물 1

HCID 1009552',4'-Difluoro(1,1'-biphenyl)-4-ol수율 109.6%

시약·촉매·용매 3

HCID 2734559Bis(tricyclohexylphosphine) palladium(0)촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

2,4-Difluoro-phenyl-boronic acid (1.29 g, 8.18 mmol) and 4-iodophenol (0.60 g, 2.7 mmol) were suspended in DMF (60 mL) and 6 mL H2O (6 mL). The mixture was degassed with nitrogen. Finely ground potassium carbonate (1.13 g, 8.18 mmol) and bis(tricyclohexylphosphine) palladium(0) (91 mg, 0.13 mmol) were added. The reaction was stirred at reflux overnight under nitrogen and cooled. The mixture was filtered through a plug of silica gel/Celite and evaporated. The residue was diluted with ethyl acetate and washed with saturated sodium bicarbonate (2×20 mL), dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography, eluting with 0-25% ethyl acetate in hexanes to yield 2′,4′-difluoro-biphenyl-4-ol (0.61 g, 100%). LR-MS (ES) calculated for C12H8F2O, 206.19; found m/z 205 [M−H]−.

후처리

  1. customThe mixture was degassed with nitrogen
  2. temperatureat reflux overnight under nitrogen
  3. temperaturecooled
  4. filtrationThe mixture was filtered through a plug of silica gel/Celite
  5. customevaporated
  6. additionThe residue was diluted with ethyl acetate
  7. washwashed with saturated sodium bicarbonate (2×20 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product was purified by flash chromatography
  12. washeluting with 0-25% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-e1b4485cb6f84a0d82965dc3d4df1593
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939569B1

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