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Potassium Carbonate → 2,3,5,6-Tetrafluoro-4-(3'-methoxyphenyl)aniline

HRID 1270717
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1270717
[F:1][C:2]1[C:8]([F:9])=[C:7](Br)[C:6]([F:11])=[C:5]([F:12])[C:3]=1[NH2:4].[CH3:13][O:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[C:8]([F:9])=[C:7]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([O:14][CH3:13])[CH:20]=2)[C:6]([F:11])=[C:5]([F:12])[C:3]=1[NH2:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 6186714-Bromo-2,3,5,6-tetrafluoroanilineHCID 2734370(3-Methoxyphenyl)boronic acid

Produkt 1

HCID 184514892,3,5,6-Tetrafluoro-4-(3'-methoxyphenyl)aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845
palladium(II) acetate
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Alternative procedure: 2,3,5,6-Tetrafluoro-4-bromoaniline (12.0 g, 49.2 mmol) is dissolved in DME (250 mL) and treated with 3-methoxyphenylboronic acid (7.5 g, 49.2 mmol), a catalytic amount of palladium(II) acetate (0.23 g, 1.0 mmol) and tri-o-tolylphosphine (1.22 g, 4.0 mmol). Potassium carbonate (13.6 g in 50 mL water) is added and the reaction mixture stirred, purged with nitrogen, then heated to 90° C. for 24 hours. After cooling to room temperature most of the DME is removed by rotary evaporator under high vacuum. The resulting material is partitioned between EtOAc (200 mL) and water (250 mL). The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator. The crude reaction product is purified by flash chromatography (9:1 hexanes/EtOAc, then 6:4 hexanes/EtOAc) to give 2,3,5,6-tetrafluoro-4-(3′-methoxyphenyl)aniline (m.p. 94–96° C.).

Aufarbeitung

  1. custompurged with nitrogen
  2. temperatureAfter cooling to room temperature most of the DME
  3. customis removed by rotary evaporator under high vacuum
  4. customThe resulting material is partitioned between EtOAc (200 mL) and water (250 mL)
  5. washThe organic layer is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by rotary evaporator
  8. customThe crude reaction product
  9. customis purified by flash chromatography (9:1 hexanes/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-2811fa6bb2e04daaa00cb5e2387f1aa1
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07202364B2

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