반응 #633445

반응 방정식

2-chloro-benzenethiol

sodium hydride

cyclopentyl bromide

→

1-chloro-2-cyclopentylsulfanyl-benzene

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   기타In a sealed tube fitted with a septum
2. 2
   workup.ADDITIONAfter addition
3. 3
   기타the tube placed in an oil bath
4. 4
   온도heated to 100° C. for 20 h
5. 5
   온도After such time the reaction mixture is cooled to 25° C.
6. 6
   workup.ADDITIONpoured
7. 7
   기타onto crushed ice
8. 8
   추출extracted with diethyl ether
9. 9
   세척The combined organic layers are then washed with a saturated aqueous solution of sodium bicarbonate
10. 10
    건조dried over sodium sulfate
11. 11
    농축concentrated in vacuo
12. 12
    workup.DISTILLATIONThe resulting liquid is then distilled

실험 절차

In a sealed tube fitted with a septum to allow for the contents to be placed under an argon atmosphere is placed 2-chloro-benzenethiol (20 mmol) and N,N-dimethylformamide (15 mL). To this solution under argon is then added in small portions sodium hydride (1.1 equiv.). After addition is complete the reaction mixture is stirred for another 20 min at 25° C. To this solution is then added cyclopentyl bromide (1.1 equiv) and the reaction is then sealed and the tube placed in an oil bath and heated to 100° C. for 20 h. After such time the reaction mixture is cooled to 25° C. and then poured onto crushed ice and extracted with diethyl ether. The combined organic layers are then washed with a saturated aqueous solution of sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. The resulting liquid is then distilled to yield 1-chloro-2-cyclopentylsulfanyl-benzene.

출처