Dimethylformamide → 2-(4-Bromophenyl)-2-methylpropanenitrile

HRID 247145

Reaktionsgleichung

Reaktionsgleichung von HRID 247145
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#N)=[CH:6][CH:5]=1.I[CH3:14].C[N:16]([CH3:19])C=O>O>[CH3:14][C:10]([C:7]1[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][CH:6]=1)([CH3:11])[C:19]#[N:16]

Komponenten

6

Edukt 4

HCID 6228Dimethylformamide3×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27914Benzeneacetonitrile, 4-bromo-

Produkt 1

HCID 104435912-(4-Bromophenyl)-2-methylpropanenitrileAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (60% dispersion in oil, 50 g, 1.25 m) in dry N,N-dimethylformamide (400 ml under nitrogen was added with stirring a solution of 4-bromophenylacetonitrile in N,N-dimethylformamide (400 ml) keeping the temperature between 30° and 40° C. A solution of iodomethane (213 g, 1.50 m) in N,N-dimethylformamide was then added gradually keeping the temperatue between 35° C. and the mixture then stirred at ambient temperature overnight. With ice cooling 2N aqueous hydrochloric acid (800 ml) was gradually added and then the mixture was diluted with water (1200 ml). The product was extracted with ether and the extract washed with water, saturated sodium bicarbonate, aqueous sodium sulphite, water again and finally brine. After drying and concentration on vacuo an orange oil was obtained which was distilled in vacuo to give the title compound as a colourless liquid (98.05 g, 87.5%) b.pt. 98°-100°/0.4 mm.

Aufarbeitung

  1. additionwas added
  2. customthe temperature between 30° and 40° C
  3. custombetween 35° C.
  4. extractionThe product was extracted with ether
  5. washthe extract washed with water, saturated sodium bicarbonate, aqueous sodium sulphite, water again
  6. customAfter drying
  7. concentrationconcentration on vacuo an orange oil
  8. customwas obtained which
  9. distillationwas distilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-871b5928d41841faa5759a279af95522
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705854

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