Hydrogen Peroxide → 2-fluoro-4-(4-methoxyphenyl)benzonitrile

HRID 466483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 466483
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([F:21])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].OO>C(O)C.C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[C:17]([C:16]1[CH:19]=[CH:20][C:13]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:14][C:15]=1[F:21])#[N:18]

Komponenten

8

Edukt 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 7360294-Bromo-2-fluorobenzonitrile

Produkt 1

HCID 27633572-fluoro-4-(4-methoxyphenyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 241BenzeneLösungsmittelHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
2 °C

Versuchsvorschrift

A solution of compound 1 (10.64 g, 0.07 mol) in ethanol (90 ml) was added dropwise to a stirred mixture of compound 3 (12.0 g, 0.06 mol) and tetrakis(triphenylphosphine)palladium(O) (2.10 g, 1.82 mmol) in benzene (125 ml) and 2M-sodium carbonate (100 ml) at room temperature under dry nitrogen. The stirred mixture was heated under reflux (90°-95° C.) for 2.5 h (i.e., until glc analysis revealed absence of starting material). The mixture was cooled and stirred for 1 h at room temperature with 30% hydrogen peroxide (2 ml). The mixture was cooled further to 2° C., the product was filtered off and washed with water. The product was dried (CaCl2) in vacuo to give a yellow powder.

Aufarbeitung

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux (90°-95° C.) for 2.5 h (i.e., until glc analysis revealed absence of starting material)
  3. temperatureThe mixture was cooled
  4. filtrationthe product was filtered off
  5. washwashed with water
  6. dry with materialThe product was dried (CaCl2) in vacuo
  7. customto give a yellow powder

Quellen und Nachweise

ORD-Eintrag
ord-b54d637471d4469b89e7e20e7568fcc3
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05156763

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