1,2-Dibromoethane → 1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-

HRID 45634

Reaktionsgleichung

Reaktionsgleichung von HRID 45634
[Br:1][CH2:2][CH2:3]Br.[C:5]1(=[O:15])[NH:9][C:8](=[O:10])[C:7]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:6]12.[K]>CN(C)C=O>[Br:1][CH2:2][CH2:3][N:9]1[C:5](=[O:15])[C:6]2[C:7](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8]1=[O:10]

Komponenten

4

Edukt 2

HCID 78391,2-DibromoethaneHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Into a 500-mL round-bottom flask, was placed a solution of 1,2-dibromoethane (30 g, 159.57 mmol, 2.95 equiv) in N,N-dimethylformamide (200 mL). This was followed by the addition of potassium phthalimide (10 g, 54.05 mmol, 1.00 equiv) in several batches. The resulting solution was stirred for 24 h at 60° C. The reaction was then quenched by the addition of 500 mL of water. The resulting solution was extracted with 2×200 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). This resulted in 8 g (57%) of 2-(2-bromoethyl)isoindoline-1,3-dione as a white solid.

Aufarbeitung

  1. customInto a 500-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of 500 mL of water
  3. extractionThe resulting solution was extracted with 2×200 mL of ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 8 g (57%) of 2-(2-bromoethyl)isoindoline-1,3-dione as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-d52e8b04a6564edfa0274bb3abd45132
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541448B2

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