Ammonium Chloride → HCID 67002199, Verbindung

HRID 558440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 558440
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:18]=[CH:17][C:7]([CH2:8]P(=O)(OCC)OCC)=[CH:6][CH:5]=1.[Br:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][C:23]=1[CH:30]=O.CC(C)([O-])C.[K+].[Cl-].[NH4+]>CN(C=O)C.O>[Br:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][C:23]=1[CH:30]=[CH:8][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:19])[F:20])=[CH:18][CH:17]=1

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 225749024-Bromo-3-formylbenzonitrileHCID 23665647Potassium tert-butoxideHCID 57744084HCID 57744084, Verbindung

Produkt 1

HCID 67002199HCID 67002199, VerbindungAusbeute 44,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
-25 °C

Versuchsvorschrift

Diethyl (4-trifluoromethoxybenzyl)phosphonate (7.8 g) was dissolved in 100 mL of DMF, 5.0 g of 4-bromo-3-formyl-benzonitrile was added, and the mixture was cooled to −25° C. Potassium tert-butoxide (6.4 g) was added, and the mixture was stirred for 2 hours at −25° C. To the reaction mixture, 100 mL of a saturated aqueous solution of ammonium chloride and 100 mL of water were added, and the mixture was extracted 3 times with ethyl acetate (100 mL). The respective organic layers were combined, whereafter the combined organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. The magnesium sulfate was separated by filtration, and the filtrate was concentrated under reduced pressure. The residue was subjected to 100 g silica gel column chromatography to obtain 3.9 g of 4-bromo-3-[2-(4-trifluoromethoxy-phenyl)-vinyl]-benzonitrile as a crude product with the use of an eluant (ethyl acetate and n-hexane, 1:10).

Aufarbeitung

  1. extractionthe mixture was extracted 3 times with ethyl acetate (100 mL)
  2. washwas washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  4. customThe magnesium sulfate was separated by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ce0b6dcb9db348808ff8964fbd904482
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063046B2

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