N-bromobutanimide → 2-Chloro-3-cyanobenzaldehyde

HRID 489392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 489392
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[Cl:10])#[N:2].BrN1C(=[O:17])CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:10][C:4]1[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:9]=[O:17]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 145298902-Chloro-3-methylbenzonitrile

Produkt 1

HCID 119617032-Chloro-3-cyanobenzaldehydeAusbeute 107,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-3-methylbenzaldehyde (19.4 g) in ethanol (45 ml) was added an aqueous hydroxylamine hydrochloride (9.7 g) solution (12 ml), and an aqueous sodium hydroxide (6.9 g) solution (10 ml) was added. The mixture was stirred at room temperature for 1.5 hours. Water (500 ml) was added and the precipitated crystals were collected by filtration. The obtained white crystals (16.1 g) were dissolved in acetic anhydride (50 ml) and the mixture was heated under reflux for 2.5 hours. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (5:1)) to give 2-cyano-6-methylchlorobenzene (10.9 g) as a white solid. A suspension of 2-cyano-6-methylchlorobenzene (10.9 g), N-bromosuccinimide (12.8 g) and benzoyl peroxide (523 mg) in carbon tetrachloride (100 ml) was heated under reflux for 3.5 hours. The insoluble material was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (20:1)) to give 2-chloro-3-cyanobenzaldehyde (12.8 g) as a colorless oil. Subsequently, the title compound was prepared from 2-chloro-3-cyanobenzaldehyde, 3-aminopyrazole and ethyl 3-ketohexanoate in the same manner as in Example 25.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 3.5 hours
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate (20:1))

Quellen und Nachweise

ORD-Eintrag
ord-4383f4de93354737b0e3a327baccbf15
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06977262B2

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