2-Bromo-1-(3,4-dichlorophenyl)ethanone → HCID 178477975, Verbindung

HRID 276771

Reaktionsgleichung

Reaktionsgleichung von HRID 276771
C[Si](C)(C)[N-:3][Si](C)(C)C.[Li+].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][N:13]=1.C(=O)(O)[O-].[Na+].[Cl:25][C:26]1[CH:27]=[C:28]([CH:33]=[CH:34][C:35]=1[Cl:36])[C:29](=O)[CH2:30]Br>C1COCC1.C(Cl)(Cl)Cl.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[NH:3][CH:30]=[C:29]([C:28]3[CH:33]=[CH:34][C:35]([Cl:36])=[C:26]([Cl:25])[CH:27]=3)[N:19]=2)=[CH:14][N:13]=1

Komponenten

8

Edukt 4

HCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanoneHCID 516892Sodium BicarbonateHCID 2733832Lithium HexamethyldisilazideHCID 51520946-Chloro-3-pyridinecarbonitrile

Produkt 1

HCID 178477975HCID 178477975, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Lithium hexamethyldisilazide (41.5 mL of a 1.0 M solution in THF) was added to a solution of 2-chloro-5-cyanopyridine (5.24 g) in THF (10 mL). The resultant mixture was stirred at room temperature for 30 min, and then 13 mL saturated aqueous sodium bicarbonate and 5 mL water were added to the reaction mixture. A solution of 3,4-dichlorophenacyl bromide (10.13 g) in chloroform (150 mL) was added in two portions approximately 15 min apart. The resultant mixture was stirred for 72 hours, and the reaction mixture was filtered. The filter cake was triturated with dichloromethane (50 mL) to provide 2-Chloro-5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridine (10.46 g). MS m/z 324 (M+), 326 (M++2).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. customThe filter cake was triturated with dichloromethane (50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-ee9b6e165ef34b6fb9cf15324b2925e1
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355635B1

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