Cesium fluoride → 2-fluoro-4-phenylbenzonitrile

HRID 583840Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583840
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F-].[Cs+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:10][C:4]1[CH:3]=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Komponenten

6

Edukt 3

HCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 7360294-Bromo-2-fluorobenzonitrile

Produkt 1

HCID 27633602-fluoro-4-phenylbenzonitrileAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 4-bromo-2-fluorobenzonitrile (1.12 g, 5.6 mmol) in 1,2-dimethoxyethane (10 mL) were added Phenyl boronic acid (750 mg, 6.16 mmol), tetrakis(triphenylphosphine)palladium (0) (194 mg, 0.17 mmol) and Cesium fluoride (1.8 g, 12.3 mmol). The mixture of reaction was stirred at 100° C. under nitrogen for 3 h. Then, the mixture is cooled and filter through celite. Then added ethyl acetate and water and extracted (3×). The crude was purified by chromatography (silica gel, hexane-ethyl acetate 10:1) affordind 818 mg (74% yield)n of the title compound.

Aufarbeitung

  1. additionThe mixture of reaction
  2. temperatureThen, the mixture is cooled
  3. filtrationfilter through celite
  4. extractionThen added ethyl acetate and water and extracted (3×)
  5. customThe crude was purified by chromatography (silica gel, hexane-ethyl acetate 10:1) affordind 818 mg (74% yield)n of the title compound

Quellen und Nachweise

ORD-Eintrag
ord-6b0fab5263ea40428287798687af65bc
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924294B2

Notizen zur Reaktion

Wird geladen…