Hydrochloric Acid → 3-Chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile

HRID 353604

Reaktionsgleichung

Reaktionsgleichung von HRID 353604
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[Cl:10][CH2:11][C:12]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].Cl>C1(C)C=CC=CC=1>[Cl:10][CH2:11][C:12]1[CH:20]=[C:19]([CH:18]=[CH:17][C:13]=1[C:14](=[O:15])[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:21]#[N:22]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 113449102-(Chloromethyl)-4-cyanobenzoyl chlorideHCID 178418676HCID 178418676, Verbindung

Produkt 1

HCID 99434343-Chloromethyl-4-(4-fluoro-benzoyl)-benzonitrileAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 4-fluoro phenylmagnesium bromide (0.73M in THF, 170 ml) was added to a cooled solution of 2-chloromethyl-4-cyano-benzoyl chloride (25.0 g) in toluene (200 ml) so that the temperature did not raise above 0° C. The mixture was stirred at 0° C. for 2 hours. An aqueous solution of HCl (250 ml) was added and stirring continued for 0.5 hours. The phases were separated and the aqueous phase was extracted with toluene (200 ml). The combined organic phases were washed with saturated NaHCO3 solution (200 ml) and water (100 ml). The solvents were evaporated in vacuo to give a brownish oil (29.0 g, 90%). Spectral and analytical data were in accordance with the example above.

Aufarbeitung

  1. temperaturedid not raise above 0° C
  2. stirringstirring
  3. waitcontinued for 0.5 hours
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with toluene (200 ml)
  6. washThe combined organic phases were washed with saturated NaHCO3 solution (200 ml) and water (100 ml)
  7. customThe solvents were evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fe7731d6d3114efab715343d7bc05b64
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06753433B2

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