Reaktion #74444

Reaktionsgleichung

5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole

tert-butyl bromoacetate

→

title compound

Tert-butyl[5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindol-5-yl]acetate

Lösungsmittel

THF

cyclohexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturcooling bath
3. 3
   Sonstigewas removed
4. 4
   SonstigeAfter 1.5 h the reaction was quenched with aqueous saturated NH4Cl and layers
5. 5
   Sonstigewere separated
6. 6
   ExtraktionAqueous layer was extracted with EtOAc (2×)
7. 7
   TrocknenCombined organic layers were dried over Na2SO4
8. 8
   Einengenconcentrated

Vorschrift

To a solution of 5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole (3.17 g) in THF (60 mL) at −78° C. was added LAD solution (10.19 mL, 1.5 M in cyclohexane) drop wise. After stirring for 5 minutes tert-butyl bromoacetate was added, cooling bath was removed and the reaction mixture was stirred at room temperature. After 1.5 h the reaction was quenched with aqueous saturated NH4Cl and layers were separated. Aqueous layer was extracted with EtOAc (2×). Combined organic layers were dried over Na2SO4 and concentrated. Flash chromatography using a linear gradient of 1-50% EtOAc in hexanes afforded title compound as a white solid. Mass. found (M+H)+, 427.0.

Quelle