Ethanol → 2-Chloro-6-ethoxybenzonitrile

HRID 1158826

Reaktionsgleichung

Reaktionsgleichung von HRID 1158826
CC[CH2:3][CH2:4][O-:5].[Na+].C(O)C.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15](F)[C:12]=1[C:13]#[N:14].C(Cl)(Cl)Cl>C1COCC1.O>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([O:5][CH2:4][CH3:3])[C:12]=1[C:13]#[N:14]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 6212ChloroformHCID 695872-Chloro-6-fluorobenzonitrileHCID 23669364Sodium n-butylate

Produkt 1

HCID 222709292-Chloro-6-ethoxybenzonitrileAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of sodium 1-butoxide (65 g, 0.642 mol) in THF (1 L), at room temperature under a dry nitrogen atmosphere, ethanol (250 mL, 5.35 mol) was added over a 10 minute period. To the resulting solution, 2-chloro-6-fluorobenzonitrile (100 g, 0.642 mol) was added in portions. The reaction mixture was stirred at room temperature for 30 minutes and then reduced to a volume of approximately 250 mL under reduced pressure. The resulting mixture was poured into chloroform and water and the layers separated. The organic layer was washed with water (twice) and brine, dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure to afford a light yellow solid. This material was recrystallized from hexanes to provide the 2-chloro-6-ethoxybenzonitrile, 135, (101 g, 87% yield) as a white crystalline solid.

Aufarbeitung

  1. customthe layers separated
  2. washThe organic layer was washed with water (twice) and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto afford a light yellow solid
  7. customThis material was recrystallized from hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d43f8b5cf77542039d4ba795f215839f
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07812038B2

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