반응 #68496

반응 방정식

4-chloro-2-fluoro-1-iodobenzene

pyrrolidin-2-one

(1R,2R)-cyclohexane-1,2-diamine

potassium phosphate

1,4-dioxane

→

1-(4-chloro-2-fluorophenyl)pyrrolidin-2-one

수율 108.4%

반응 조건

후처리

1. 1
   기타A 100 mL sealed tube
2. 2
   기타flushed with argon
3. 3
   기타sealed
4. 4
   기타placed in a 110° C.
5. 5
   기타for 17 hours
6. 6
   여과The reaction mixture was filtered through a pad of silica gel
7. 7
   세척eluting with EtOAc and DCM
8. 8
   농축the filtrate was concentrated
9. 9
   기타to yield a brown oil
10. 10
    기타This was purified by column chromatography
11. 11
    세척eluting with a gradient of 3-5% MeOH/DCM over 30 minutes

실험 절차

A 100 mL sealed tube was charged with 4-chloro-2-fluoro-1-iodobenzene (0.498 ml, 3.90 mmol), pyrrolidin-2-one (0.598 ml, 7.80 mmol), (1R,2R)-cyclohexane-1,2-diamine (0.0703 ml, 0.585 mmol), potassium phosphate (1.66 g, 7.80 mmol), copper (I) iodide (0.0223 g, 0.117 mmol), and 1,4-dioxane (4.00 ml, 46.8 mmol), then flushed with argon, sealed, and placed in a 110° C. oil bath for 17 hours. The reaction mixture was filtered through a pad of silica gel, eluting with EtOAc and DCM, then the filtrate was concentrated to yield a brown oil This was purified by column chromatography using a 40 g ISCO column, eluting with a gradient of 3-5% MeOH/DCM over 30 minutes to give 1-(4-chloro-2-fluorophenyl)pyrrolidin-2-one (0.903 g, 108% yield) as a yellow solid.

출처