4-Iodophenol → 4',5'-Difluoro-2'-methoxy-biphenyl-4-ol

HRID 547844노트

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HRID 547844 반응식
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5](B(O)O)=[C:4]([O:12][CH3:13])[CH:3]=1.I[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[C:4]([O:12][CH3:13])[CH:3]=1

참가 물질

8

반응물 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 16217679(4,5-Difluoro-2-methoxyphenyl)boronic acid

생성물 1

HCID 582599934',5'-Difluoro-2'-methoxy-biphenyl-4-ol수율 89.3%

시약·촉매·용매 4

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
82.5 °C

실험 절차

4,5-Difluoro-2-methoxyphenyl-boronic acid (8.8 g, 46.82 mmol) and 4-iodophenol (6.86 g, 31.21 mmol) were suspended in 165 ml of DMF. H2O (40 mL) was added and the mixture was degassed with argon. Finely ground potassium carbonate (13 g, 93.63 mmol) and tetrakis(triphenylphosphine) palladium(0) (1.5 g, 1.29 mmol) were added. The reaction was stirred at 80-85° C. for 1 hr under argon and cooled. The mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried and solvents were evaporated. The crude product was purified by flash chromatography, eluting with 0-8% ethyl acetate in hexanes to yield 4′,5′-difluoro-2′-methoxy-biphenyl-4-ol (6.58 g, 89.3%). LR-MS (ES) calculated for C13H10F2O, 236.22; found m/z 235 [M−H]−.

후처리

  1. customthe mixture was degassed with argon
  2. temperaturecooled
  3. washThe organic layer was washed with brine
  4. customdried
  5. customsolvents were evaporated
  6. customThe crude product was purified by flash chromatography
  7. washeluting with 0-8% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-ca1b55e1aeb742eca7e378533e6547e1
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939569B1

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