Allyl bromide → 3-Methoxy-4-chloro-benzoic acid allyl ester

HRID 500603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500603
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[Cl:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=1[O:21][CH3:22]>CN(C)C=O>[CH2:7]([O:18][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][C:12]([Cl:11])=[C:13]([O:21][CH3:22])[CH:14]=1)[CH:8]=[CH2:9]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 20633784-Chloro-3-methoxybenzoic acid

Produkt 1

HCID 674384813-Methoxy-4-chloro-benzoic acid allyl esterAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium carbonate (4.44 g, 32.156 mmol) and allyl bromide (2.78 ml, 32.156 mmol) were added to a stirred solution of 4-chloro-3-methoxybenzoic acid (3 g, 16.078 mmol) in N,N-dimethylformamide (30 ml) and allowed to stir at room temperature for 18 hours. The reaction mixture was partitioned between diethyl ether (200 ml) and water (150 ml), the organic phase extracted and further washed with water (150 ml), dried over sodium sulfate and concentrated in vacuo to afford the title compound as an orange oil in 98% yield, 3.57 g.

Aufarbeitung

  1. customThe reaction mixture was partitioned between diethyl ether (200 ml) and water (150 ml)
  2. extractionthe organic phase extracted
  3. washfurther washed with water (150 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-54cf94ea73e14c4fb2f4aa8e1f0f6972
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772223B2

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