Reaktion #73802

Reaktionsgleichung

(4-Bromo-phenyl)-(4-chloro-phenyl)-methanol

N-(2-hydroxyethyl)phthalimide

para-toluenesulfonic acid monohydrate

→

title compound

Ausbeute 56.3%

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

Ausbeute 56.3%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux under Dean-Stark conditions for 17 hours
3. 3
   TemperaturUpon cooling
4. 4
   Sonstigethe solvent was removed
5. 5
   Sonstigethe residue was partitioned between ethyl acetate and water
6. 6
   TrocknenThe organic layer was then dried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe crude product was purified by column chromatography (SiO2)
10. 10
    Wascheneluting with ethyl acetate/petroleum ether (1:4)

Vorschrift

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.

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