تفاعل #9408

معادلة التفاعل

spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one

sodium acetate

bromine

→

subtitled compound

المردود 67.0%

5′-Bromospiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one

المردود 67.0%

المذيبات

acetic acid

ظروف التفاعل

المعالجة

1. 1
   أخرىthe reaction mixture was partitioned between water and EtOAc
2. 2
   استخلاصThe aqueous phase was extracted twice with EtOAc
3. 3
   غسيلThe combined organic layers were washed with water
4. 4
   تجفيفdried (MgSO4)
5. 5
   أخرىevaporated
6. 6
   أخرىthe residue was triturated with hexane
7. 7
   أخرىThe precipitate was collected
8. 8
   أخرىdried in vacuo

الإجراء التجريبي

To a solution of spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one (17.6 g, 0.09 mol) in acetic acid (300 cm3) was added sodium acetate (8.0 g, 0.1 mol) and bromine (14.6 g, 0.091 mol) with stirring. After 30 min. at room temperature, the reaction mixture was partitioned between water and EtOAc. The aqueous phase was extracted twice with EtOAc. The combined organic layers were washed with water, dried (MgSO4) and evaporated and the residue was triturated with hexane. The precipitate was collected, and dried in vacuo to obtain the subtitled compound (16.5 g, 67%) as off-white crystals: mp 196–199° C.; 1H NMR (DMSO-d6) δ 1.62 (m, 10H), 6.8 (d, 1H, J=6.8 Hz), 7.36 (d, 1H, J=8.2, 1.8 Hz), 7.58 (dd, 1H, J=8.2, 1.8 Hz), 10.44 (s, 1H).

المصدر