Hydrochloric Acid → 3',5'-Dichloroacetophenone

HRID 1350097

Reaktionsgleichung

Reaktionsgleichung von HRID 1350097
CI.[Mg].[Cl:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([Cl:13])[CH:12]=1)C#N.Cl.CC[O:17][CH2:18][CH3:19]>C1C=CC=CC=1.O>[Cl:4][C:5]1[CH:6]=[C:7]([C:18](=[O:17])[CH3:19])[CH:10]=[C:11]([Cl:13])[CH:12]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether4×HCID 6328Methyl iodideHCID 810523,5-DichlorobenzonitrileHCID 5462224Magnesium

Produkt 1

HCID 27580583',5'-Dichloroacetophenone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of methyl iodide (4 mL) in anhydrous Et2O (40 mL) was dropped into a suspension of magnesium (1.6 g) in anhydrous Et2O (16 mL) under a Nitrogen atmosphere. At the end of the dropping, benzene (120 mL) was added and the Et2O eliminated with a Nitrogen flux. Then, a solution of 3,5-dichlorobenzonitrile (4 g) in benzene (48 mL) was added and the mixture was heated to reflux for 3 hours. The solution was cooled to 0° C. and a 6N hydrochloric acid solution was added and the mixture was stirred overnight at r.t. Water and Et2O were added and the layers were separated. The organic phase was washed with a saturated sodium hydrogen carbonate solution and brine, dried and concentrated in vacuo. The residue was purified by flash chromatography (CH/AcOEt 95:5) to give the title compound (2.55 g) as an orange oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customthe layers were separated
  4. washThe organic phase was washed with a saturated sodium hydrogen carbonate solution and brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (CH/AcOEt 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-6242f81b8dbc4a129f3e525f0c94c963
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07214680B2

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