تفاعل #48531

معادلة التفاعل

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

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was cooled to −70° C.
2. 2
   workup.STIRRINGThe mixture was stirred overnight at r.t
3. 3
   استخلاصThe separated aqueous layer was extracted with EtOAc three times
4. 4
   غسيلThe combined extracts were washed with water
5. 5
   أخرىdried
6. 6
   أخرىevaporated
7. 7
   أخرىThe crude product was purified by silica gel chromatography first
8. 8
   أخرىpurified by prep HPLC

الإجراء التجريبي

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).

المصدر