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

HRID 1270716
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1270716
[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(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC>[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

6

Edukt 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 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 1

HCID 8071
1,2-Dimethoxyethane
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2,3,5,6-Tetrafluoro-4-bromoaniline (7.5 g, 30.7 mmol) is dissolved in DME (150 mL) and treated with 3-methoxyphenylboronic acid (4.7 g, 30.7 mmol), a catalytic amount of tetrakistriphenylphosphine palladium(0) (0.70 g, 0.6 mmol) and triphenylphosphine (0.66 g, 2.5 mmol). Potassium carbonate (8.5 μg in 50 mL of water) is added and the reaction mixture stirred and 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. customis removed by rotary evaporator under high vacuum
  2. customThe resulting material is partitioned between EtOAc (200 mL) and water (250 mL)
  3. washThe organic layer is washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by rotary evaporator
  6. customThe crude reaction product
  7. customis purified by flash chromatography (9:1 hexanes/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-c0a8c1fe4a3c4fe9b0f239282dd887b2
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07202364B2

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