Ammonium Chloride → 3-Chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile

HRID 353602

Reaktionsgleichung

Reaktionsgleichung von HRID 353602
[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-].[NH4+].C(OCC)(=O)C.CCCCCC>O1CCCC1>[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

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 113449102-(Chloromethyl)-4-cyanobenzoyl chlorideHCID 21226206Ethyl acetate hexaneHCID 178418676HCID 178418676, Verbindung

Produkt 1

HCID 99434343-Chloromethyl-4-(4-fluoro-benzoyl)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 4-fluoro phenylmagnesium bromide (3.76 g) in tetrahydrofuran (15 ml) was added to a cooled solution of 2-chloromethyl-4-cyano-benzoyl chloride (3.95 g) in tetrahydrofuran (10 ml) so that the temperature did not raise above 0° C. The mixture was warmed slowly to room temperature and stirred over night. Saturated ammonium chloride solution (60 ml) was added and stirring continued for 0.5 hours. The phases were separated and the aqueous phase was extracted with diethylether (30 ml). The combined organic phases were dried over sodium sulfate, filtered and dried in vacuo to give a brown solid. Flash chromatography (ethyl acetate/n-hexane=1/10) provided the product as colourless solid. Yield 2.95 g, 58%. 1H NMR (CDCl3, 400 MHz): 4.71 (2H, s), 7.16-7.21 (2H, m), 7.46 (1H, d, J=7.9 Hz), 7.71 (1H, dd, J=1.5, 7.9 Hz), 7.81-7.86 (2H, m), 7.89 (1H, d, J=1.5 Hz). 13C NMR (CDCl3, 100 MHz): 42.3, 115.0, 116.4, 116.6, 117.9, 129.6, 132.95, 132.98, 133.4, 133.5, 134.3, 138.7, 142.4, 165.5, 168.1, 194.5.

Aufarbeitung

  1. temperaturedid not raise above 0° C
  2. stirringstirring
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with diethylether (30 ml)
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. customdried in vacuo
  8. customto give a brown solid

Quellen und Nachweise

ORD-Eintrag
ord-e922eef638ad42aaa2bcc784d588c265
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06753433B2

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