Potassium Carbonate → 2-[(2-Chloro-4-nitrophenoxy)methyl]-6-methylpyridine

HRID 222035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222035
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1F>CC#N>[Cl:16][C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1[O:9][CH2:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 707366-Methyl-2-pyridylmethanol

Produkt 1

HCID 668773902-[(2-Chloro-4-nitrophenoxy)methyl]-6-methylpyridineAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To 35 mL CH3CN was added (6-Methyl-pyridin-2-yl)-methanol (3.5 g, 28.4 mmol), followed by potassium carbonate (17.9 g, 129.6 mmol), and 2-Chloro-1-fluoro-4-nitrobenzene (6.48 g, 36.9 mmol). The suspension was stirred and heated at 70° C. for 30 h, after which time the bright yellow mixture was allowed to cool to rt. The contents were cooled to rt, filtered, and washed with CH2Cl2. The filtrate was concentrated in vacuo to a a light yellow solid which was triturated with Hex/EtOAc (5:1), yielding 2-[(2-chloro-4-nitrophenoxy)methyl]-6-methylpyridine (4.87 g, 61%) as a white solid.

Aufarbeitung

  1. temperatureto cool to rt
  2. temperatureThe contents were cooled to rt
  3. filtrationfiltered
  4. washwashed with CH2Cl2
  5. concentrationThe filtrate was concentrated in vacuo to a a light yellow solid which
  6. customwas triturated with Hex/EtOAc (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-41c2a8d20bc14c2096ceb9be589da0ec
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207172B2

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