Potassium Cyanide → 2-Chloro-6-iodobenzeneacetonitrile

HRID 2078341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2078341
Br[CH2:2][C:3]1[C:8]([I:9])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:10].[C-:11]#[N:12].[K+]>CCO.O>[Cl:10][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([I:9])[C:3]=1[CH2:2][C:11]#[N:12]

Komponenten

5

Edukt 2

HCID 9032Potassium CyanideHCID 670999852-(Bromomethyl)-1-chloro-3-iodobenzene

Produkt 1

HCID 670998812-Chloro-6-iodobenzeneacetonitrileAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-(bromomethyl)-1-chloro-3-iodobenzene (14 g, 42 mmol) in 100 mL EtOH was treated with a solution of potassium cyanide (3.6 mL, 84 mmol) in 40 mL water. The mixture was refluxed for 2.5 hours. The mixture was cooled to room temperature and then concentrated. The residue was diluted with 200 mL EtOAc, washed with water (2×50 mL), saturated NaCl (50 mL), dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (20% EtOAc/hexane) to give 10.18 g pale yellow solid. MS m/e: (M−1)− 276.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2.5 hours
  2. concentrationconcentrated
  3. additionThe residue was diluted with 200 mL EtOAc
  4. washwashed with water (2×50 mL), saturated NaCl (50 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (20% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-83c5d84623fb4c1191dccf49c1a479b1
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928139B2

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