تفاعل #1680796

معادلة التفاعل

ethyl 4-bromo-3-oxocyclohexanecarboxylate

4-fluorobenzenethiol

KOH

→

title compound

المردود 51.0%

Ethyl 4-[(4-fluorophenyl)thio]-3-oxocyclohexanecarboxylate

المردود 51.0%

المذيبات

EtOH

EtOH

ظروف التفاعل

المعالجة

1. 1
   ترشيحthen filtered
2. 2
   تركيزThe filtrate was concentrated in vacuo
3. 3
   workup.ADDITIONthen diluted with water
4. 4
   استخلاصextracted with diethyl ether
5. 5
   غسيلThe organic layer was washed with water
6. 6
   تجفيفbrine, then was dried over MgSO4
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىPurification by chromatography on silica gel (15% EtOAc in hexane)

الإجراء التجريبي

To a solution of ethyl 4-bromo-3-oxocyclohexanecarboxylate (5.2 g, 20.9 mmol) in EtOH (120 mL) at 80° C. was added a solution of 4-fluorobenzenethiol (2.22 mL, 20.9 mmol) and KOH (1.29 g, 22.9 mmol) in EtOH (50 mL). The suspension was stirred for 30 min then filtered. The filtrate was concentrated in vacuo then diluted with water and extracted with diethyl ether. The organic layer was washed with water then brine, then was dried over MgSO4 and concentrated in vacuo. Purification by chromatography on silica gel (15% EtOAc in hexane) afforded the title compound (3.08 g, 51%) as a white solid: mp 96-97° C.; MS (+) 297 (M+H)+.

المصدر