Triphenylphosphine → (3-(1,3-Dioxoisoindolin-2-yl)propyl)triphenylphosphonium bromide

HRID 510622

Reaktionsgleichung

Reaktionsgleichung von HRID 510622
[Br:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[Br-:1].[O:15]=[C:6]1[C:7]2[C:8](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:10])[N:5]1[CH2:4][CH2:3][CH2:2][P+:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 21611N-3-Bromopropylphthalimide

Produkt 1

HCID 22018487(3-(1,3-Dioxoisoindolin-2-yl)propyl)triphenylphosphonium bromideAusbeute 36,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of N-(3-bromopropyl)phthalimide (25.0 g, 93.2 mmol) and triphenylphosphine (24.5 g, 93.2 mmol) in toluene (200 mL) was stirred and heated to reflux for 15 hours. The reaction mixture was cooled to ambient temperature and the resulting precipitate was collected by filtration, washed with toluene, and dried under vacuum to afford (3-(1,3-dioxoisoindolin-2-yl)propyl)triphenylphosphonium bromide as a white powder (17.9 g, 36% yield).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 15 hours
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with toluene
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-86cf9f1939b74f3f9c71d517ec0c0e79
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096567B2

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