Thionyl Chloride → 2-(2-Chloroethyl)isoindolin-1-one

HRID 1764874

Reaktionsgleichung

Reaktionsgleichung von HRID 1764874
O[CH2:2][CH2:3][N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:13].S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[Cl:16][CH2:2][CH2:3][N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:13]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 2201052-(2-hydroxyethyl)-3H-isoindol-1-one

Produkt 1

HCID 27835142-(2-Chloroethyl)isoindolin-1-oneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 2-(2-hydroxyethyl)isoindolinone (1.0 g, 5.64 mmol) in toluene (3.5 mL) was added thionyl chloride (1.34 g, 11.3 mmol). The reaction mixture was stirred at 20° C. for 3 h then 4 h at 60° C. The reaction mixture was concentrated in vacuo to remove excess thionyl chloride and toluene. 2-(2-Chloroethyl)isoindolinone (1.01 g, 92%) was obtained by flash chromatography on a silica gel column by elution with EtOAc/Hexanes a white solid. 1H NMR (CDCl3, 300 MHz) δ3.81 (t, 2H, J=5.5 Hz), 3.97 (t, 2H, J=5.9 Hz), 4.59 (s, 2H), 7.44-7.58 (m, 3H), 7.86 (d, 1H, J=6.9 Hz) ppm.

Aufarbeitung

  1. custom4 h
  2. customat 60° C
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto remove excess thionyl chloride and toluene

Quellen und Nachweise

ORD-Eintrag
ord-933a6a5ec3aa4fac87abdffadc97335d
Quelldatensatz
uspto-grants-2007_06
Patentnummer
USRE039679E1

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