Water → 2-(7-Chlorobenzo[d][1,3]dioxol-5-yl)acetonitrile

HRID 503270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503270
[Cl:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[C:4]([CH2:11]Cl)[CH:3]=1.[C-:13]#[N:14].[Na+].O>CS(C)=O>[Cl:1][C:2]1[C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=[C:4]([CH2:11][C:13]#[N:14])[CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 8929Sodium CyanideHCID 162270934-Chloro-6-(chloromethyl)-1,3-dioxaindane

Produkt 1

HCID 670440102-(7-Chlorobenzo[d][1,3]dioxol-5-yl)acetonitrileAusbeute 59,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A mixture of 4-chloro-6-(chloromethyl)benzo[d][1,3]dioxole (6.0 g, 29 mmol) and NaCN (1.6 g, 32 mmol) in DMSO (20 mL) was stirred at 40° C. for 1 h and was then poured into water. The mixture was extracted with EtOAc (30 mL×3). The combined organic layers were washed with water and brine, dried over Na2SO4 and evaporated under reduced pressure to afford 2-(7-chlorobenzo[d][1,3]dioxol-5-yl)acetonitrile (3.4 g, 58%). 1H NMR δ 6.81 (s, 1H), 6.71 (s, 1H), 6.07 (s, 2H), 3.64 (s, 2H). 13C-NMR 6149.2, 144.3, 124.4, 122.0, 117.4, 114.3, 107.0, 102.3, 23.1.

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc (30 mL×3)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5942d20eaf0742bcbc9830fb968ec317
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776905B2

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