N-(2-Hydroxyethyl)phthalimide → 2-{2-[(4-Bromo-phenyl)-(4-chloro-phenyl)-methoxy]-ethyl}-isoindole-1,3-dione

HRID 45524

Reaktionsgleichung

Reaktionsgleichung von HRID 45524
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[OH:9])=[CH:4][CH:3]=1.O[CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[O:9][CH2:18][CH2:19][N:20]2[C:21](=[O:30])[C:22]3[C:23](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]2=[O:25])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 77499N-(2-Hydroxyethyl)phthalimideHCID 521998p-Toluenesulfonic acid monohydrateHCID 57659206(4-Bromophenyl)(4-chlorophenyl)methanol

Produkt 1

HCID 593319222-{2-[(4-Bromo-phenyl)-(4-chloro-phenyl)-methoxy]-ethyl}-isoindole-1,3-dioneAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of (4-Bromo-phenyl)-(4-chloro-phenyl)-methanol (2.3 g, 7.73 mmol), N-(2-hydroxyethyl)phthalimide (1.4 g, 7.36 mmol) and para-toluenesulfonic acid monohydrate (560 mg, 2.94 mmol) in toluene (50 ml) was heated to reflux under Dean-Stark conditions for 17 hours. Upon cooling, the solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was then dried (MgSO4), filtered and concentrated. The crude product was purified by column chromatography (SiO2), eluting with ethyl acetate/petroleum ether (1:4), to yield the title compound (1.95 g). LC/MS: (PS-B3) Rt 4.07 no observable mass ion.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under Dean-Stark conditions for 17 hours
  3. temperatureUpon cooling
  4. customthe solvent was removed
  5. customthe residue was partitioned between ethyl acetate and water
  6. dry with materialThe organic layer was then dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (SiO2)
  10. washeluting with ethyl acetate/petroleum ether (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-02b2cacfa25c40dc8ae5eae96b3f27ec
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541461B2

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