(1,1'-Biphenyl)-2-ol → 2-(Biphenyl-2-yloxy)-5-bromo-benzonitrile

HRID 46287

Reaktionsgleichung

Reaktionsgleichung von HRID 46287
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[C:11]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:17]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[C:7]#[N:8]

Komponenten

5

Edukt 3

HCID 7017(1,1'-Biphenyl)-2-olHCID 11430Potassium CarbonateHCID 27249005-Bromo-2-fluorobenzonitrile

Produkt 1

HCID 594365902-(Biphenyl-2-yloxy)-5-bromo-benzonitrileAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A suspension of 5-bromo-2-fluorobenzonitrile (6.48 g, 32.4 mmol), 2-phenylphenol (5.79 g, 34 mmol) and potassium carbonate (4.92 g, 35.6 mmol) in DMF (50 ml) was heated at 70° C. for 3 hours. The reaction was cooled and quenched by the addition of water (200 ml) followed by extraction with tBuOMe. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified using silica gel column chromatography (ethyl acetate:Heptane 5:95 to 15:85) to furnish 10.1 g of the desired compound. LCMS Rt=1.78 min MS m/z 349 [M]+1HNMR (d6-DMSO): δ 6.6 (m, 1H), 7.2-7.6 (m, 9H), 7.65 (m, 1H), 8.0 (m, 1H).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customquenched by the addition of water (200 ml)
  3. extractionfollowed by extraction with tBuOMe
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-c2524a5135f547338c10b1fc44b5fda2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

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