Cesium carbonate → 4-Chloro-4'-fluorobiphenyl-2-amine

HRID 922103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 922103
Br[C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH2:4].[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O>[Cl:9][C:6]1[CH:5]=[C:3]([NH2:4])[C:2]([C:14]2[CH:15]=[CH:16][C:11]([F:10])=[CH:12][CH:13]=2)=[CH:8][CH:7]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 2856454-Fluorophenylboronic acidHCID 113102762-Bromo-5-chloroaniline

Produkt 1

HCID 576671854-Chloro-4'-fluorobiphenyl-2-amineAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Bromo-5-chloroaniline (CAS#823-57-4; 5 g), 4-fluorophenylboronic acid (3.56 g) and cesium carbonate (31.6 g) were combined in THF (70 ml) and water (35 ml). The mixture was degassed by bubbling argon through the solution. After addition of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (886 mg) the reaction mixture was stirred 1 h at 80° C. in a sealed tube. The reaction mixture was diluted with EtOAc, washed with water, dried over Na2SO4, evaporated and purified by chromatography (silica gel, 0% to 30% EtOAc in heptane). The product was finally bulb-to-bulb distilled at 0.3 mbar and 120-130° C. oven temperature to give the title compound (5.07 g) as a light yellow liquid.

Aufarbeitung

  1. customThe mixture was degassed
  2. customby bubbling argon through the solution
  3. additionAfter addition of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (886 mg) the reaction mixture
  4. additionThe reaction mixture was diluted with EtOAc
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. custompurified by chromatography (silica gel, 0% to 30% EtOAc in heptane)
  9. distillationdistilled at 0.3 mbar and 120-130° C. oven temperature

Quellen und Nachweise

ORD-Eintrag
ord-a8cc7465a1084d31ab2f57396ffd0cf5
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278918B2

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