Chloroform → HCID 58155372, Verbindung

HRID 1503185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1503185
Br[CH2:2][C:3]([CH3:13])([CH3:12])[O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.[C-:14]#[N:15].[Na+].C(Cl)(Cl)Cl>CS(C)=O.[Cl-].[Na+].O>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][C:3]([CH3:13])([CH3:12])[CH2:2][C:14]#[N:15])=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 6212ChloroformHCID 8929Sodium CyanideHCID 58155366HCID 58155366, Verbindung

Produkt 1

HCID 58155372HCID 58155372, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A crude solution of 1-(2-bromo-1,1-dimethylethoxy)-4-chlorobenzene (60.3 mmol) in dimethyl sulfoxide (60 mL) is treated with sodium cyanide (180.7 mmol). The reaction mixture is heated to 95 degrees Celsius overnight under nitrogen. The reaction mixture is transferred into a separatory funnel using brine (150 mL) and chloroform (300 mL). The reaction mixture is equilibrated and the aqueous layer is removed. The aqueous layer is extracted an additional two times with chloroform (2×300 mL). The combined organic extracts are dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure to afford 3-(4-chlorophenoxy)-3-methylbutyronitrile. This crude material is used in the next step (hydrolysis of the nitrile into the corresponding amide) without further purification. [Alternatively, the corresponding carboxylic acid can be obtained from this material by acid hydrolysis (e.g., using sulfuric acid).]

Aufarbeitung

  1. temperatureThe reaction mixture is heated to 95 degrees Celsius overnight under nitrogen
  2. customThe reaction mixture is transferred into a separatory funnel
  3. customthe aqueous layer is removed
  4. extractionThe aqueous layer is extracted an additional two times with chloroform (2×300 mL)
  5. dry with materialThe combined organic extracts are dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-aea8adc281b2451981427a817469e7b0
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212155B2

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