Reaktion #48531

Reaktionsgleichung

NH4Cl

n-BuLi

1,3-dihydroindol-2-one

1-(2-bromo-ethoxy)-2,4-dichlorobenzene

→

3-[2-(2,4-dichlorophenoxy)-ethyl]-1,3-dihydroindol-2-one

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was cooled to −70° C.
2. 2
   workup.STIRRINGThe mixture was stirred overnight at r.t
3. 3
   ExtraktionThe separated aqueous layer was extracted with EtOAc three times
4. 4
   WaschenThe combined extracts were washed with water
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe crude product was purified by silica gel chromatography first
8. 8
   Sonstigepurified by prep HPLC

Vorschrift

To a suspension of 1,3-dihydroindol-2-one (13.3 g, 0.10 mol) in THF (350 mL) was added dropwise n-BuLi (2.5 M in hexane, 84.0 mL, 0.21 mol) at 0° C. under nitrogen atmosphere. After stirring for 1 h at 0° C., the reaction mixture was cooled to −70° C. and a solution of 1-(2-bromo-ethoxy)-2,4-dichlorobenzene (32.4 g, 0.12 mmol) in THF (100 mL) was added dropwise. The mixture was stirred overnight at r.t and poured into NH4Cl (aq. sat.). The separated aqueous layer was extracted with EtOAc three times. The combined extracts were washed with water, dried and evaporated. The crude product was purified by silica gel chromatography first and then purified by prep HPLC to give 3-[2-(2,4-dichlorophenoxy)-ethyl]-1,3-dihydroindol-2-one (1.9 g, 5.8% yield) as an off-white solid. 1H NMR (DMSO-d6) δ: 10.38 (s, 1H), 7.54 (d, 1H, J=2.4 Hz), 7.35 (dd, 1H, J1=8.8 Hz, J2=2.4 Hz), 7.28 (1H, J=7.2 Hz), 7.17-7.13 (m, 2H), 6.92 (t, 1H, J=7.2 Hz), 6.81 (d, 1H, J=7.6 Hz), 4.24-4.20 (m, 2H), 3.59 (t, 1H, J=6.8 Hz), 2.29-2.19 (m, 2H).

Quelle