Pyridine → 4-Bromo-4'-isopropyloxybiphenyl

HRID 2078446

Reaktionsgleichung

Reaktionsgleichung von HRID 2078446
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](O)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[Br:12][C:13]1[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].N1C=CC=CC=1>[O-2].[Cu+2].C(Cl)Cl>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:16]2[CH:17]=[CH:18][C:13]([Br:12])=[CH:14][CH:15]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 78041,4-DibromobenzeneHCID 11430Potassium CarbonateHCID 820014-Isopropoxyphenol

Produkt 1

HCID 200872814-Bromo-4'-isopropyloxybiphenylAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 164827Copper oxide (CuO)KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of Example 1A (505 mg, 3.31 mmol), 1,4-dibromobenzene (2.34 g, 9.92 mmol.), K2CO3 (960 mg, 6.87 mmol) and pyridine (20 mL) at 80° C. was added Cu(II) oxide (650 mg, 8.17 mmol). After the addition, the mixture was refluxed vigorously for 20 h. After cooling, methylene chloride was added and the mixture was filtered through Celite. The filtrate was concentrated to dryness. The residue was dissolved in ether, which was washed with 10% HCl (2×), 1N NaOH (2×), brine (1×), dried over MgSO4, and concentrated to dryness. The residue was purified on silica gel eluting with hexane and ethyl acetate gradient to give the desired product as a white solid (477 mg, 47%).

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed vigorously for 20 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite
  5. concentrationThe filtrate was concentrated to dryness
  6. dissolutionThe residue was dissolved in ether
  7. washwhich was washed with 10% HCl (2×), 1N NaOH (2×), brine (1×)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated to dryness
  10. customThe residue was purified on silica gel eluting with hexane and ethyl acetate gradient

Quellen und Nachweise

ORD-Eintrag
ord-d3ec91c6c2514aac86d7966d1b7523e5
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928243B2

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