Bromocyclopentane → HCID 67188050, compound

Temperature

25 °C

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.

1. customIn a sealed tube fitted with a septum
2. additionAfter addition
3. customthe tube placed in an oil bath
4. temperatureheated to 100° C. for 20 h
5. temperatureAfter such time the reaction mixture is cooled to 25° C.
6. additionpoured
7. customonto crushed ice
8. extractionextracted with diethyl ether
9. washThe combined organic layers are then washed with a saturated aqueous solution of sodium bicarbonate
10. dry with materialdried over sodium sulfate
11. concentrationconcentrated in vacuo
12. distillationThe resulting liquid is then distilled

ORD record

ord-24f719d9a20d43d6a8627b43215067f6

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935699B2