Dimethylformamide → 3-Phenoxy-5-(trifluoromethyl)picolinonitrile

HRID 1809597

Reaktionsgleichung

Reaktionsgleichung von HRID 1809597
Cl[C:2]1[C:3]([C:12]#[N:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.O.O.O.[O-:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Na+].CN(C=O)C>CCOCC>[O:17]([C:2]1[C:3]([C:12]#[N:13])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 14733743-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrileHCID 23681143Sodium Phenoxide Trihydrate

Produkt 1

HCID 674852863-Phenoxy-5-(trifluoromethyl)picolinonitrileAusbeute 67,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-Chloro-5-(trifluoromethyl)picolinonitrile (0.220 g, 1.07 mmol) was combined with sodium phenoxide trihydrate (0.272 g, 1.60 mmol) and DMF (5 mL). The resulting mixture was heated to 80° C. and agitated for one hour. The mixture was then cooled, diluted with ether and washed with 1M NaOH, water (3×), brine, dried and evaporated to give crude 3-phenoxy-5-(trifluoromethyl)picolinonitrile (0.190 g, 67.5% yield) as red oil.

Aufarbeitung

  1. temperatureThe mixture was then cooled
  2. washwashed with 1M NaOH, water (3×), brine
  3. customdried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-cf45a6206dbd441bbbec73d4dd1a5671
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362037B2

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