Sodium Carbonate → 3',4'-Dichloro-2-fluoro-4-methyl-biphenyl

HRID 658507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 658507
[F:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1Br.[Cl:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][C:16]=1[Cl:17].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.[Pd]>[Cl:10][C:11]1[CH:12]=[C:13]([C:7]2[CH:6]=[CH:5][C:4]([CH3:9])=[CH:3][C:2]=2[F:1])[CH:14]=[CH:15][C:16]=1[Cl:17]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 5732804-Bromo-3-fluorotolueneHCID 27343303,4-Dichlorobenzeneboronic acid

Produkt 1

HCID 669167363',4'-Dichloro-2-fluoro-4-methyl-biphenyl

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

3-fluoro-4-bromotoluene (50 g, 0.265 mol) and 3,4-dichlorophenylboronic acid (53 g, 0.278 mol) were dissolved in ethanol (970 ml) and sodium carbonate (56.1 g, 0.529 mol) was added. Palladium 10% on charcoal (6.6 g) was added, and the mixture was refluxed for 4 hours under nitrogen atmosphere. The reaction mixture was cooled, filtered and concentrated, isopropyl acetate (250 ml) was added, and then the solution was concentrated again. The residue was dissolved in isopropyl acetate (250 ml) and 1M sodium hydroxide (250 ml). The organic phase was separated, washed with water (125 ml), neutralized with hydrogen chloride 3 M, washed with brine (250 ml), and concentrated. The residue was mixed with acetonitrile/water 1/1 v/v (150 ml), heated to 40° C. to dissolve and then cooled to 0 to 5° C., and stirred for 30 minutes at this temperature. The compound 3′,4′-dichloro-2-fluoro-4-methyl-biphenyl crystallized as a powder.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 4 hours under nitrogen atmosphere
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionisopropyl acetate (250 ml) was added
  6. concentrationthe solution was concentrated again
  7. dissolutionThe residue was dissolved in isopropyl acetate (250 ml)
  8. customThe organic phase was separated
  9. washwashed with water (125 ml)
  10. washwashed with brine (250 ml)
  11. concentrationconcentrated
  12. additionThe residue was mixed with acetonitrile/water 1/1 v/v (150 ml)
  13. dissolutionto dissolve
  14. temperaturecooled to 0 to 5° C.
  15. customThe compound 3′,4′-dichloro-2-fluoro-4-methyl-biphenyl crystallized as a powder

Quellen und Nachweise

ORD-Eintrag
ord-c83d7449d98a4445bbf4c90d35771c0e
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076505B2

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