反応 #1973970

反応方程式

2-bromo-1-methoxy-4-nitrobenzene

sodium 2,2,3,3,3-pentafluoropropanoate

→

1-methoxy-4-nitro-2-(perfluoroethyl)benzene

溶媒

DMF

toluene

反応条件

後処理

1. 1
   その他to give a tan suspension
2. 2
   その他toluene was removed by a Dean-Stark trap
3. 3
   温度The mixture was heated at 155° C. for 6 h under nitrogen
4. 4
   温度cooled
5. 5
   workup.ADDITIONpoured into 100 mL of water and 100 mL of ether
6. 6
   ろ過filtered through a 1-inch plug of Celite
7. 7
   洗浄the plug was rinsed with ether
8. 8
   その他The filtrate layers were separated
9. 9
   洗浄The organic layer was washed with brine
10. 10
    乾燥dried (Na2SO4)
11. 11
    ろ過filtered
12. 12
    濃縮concentrated
13. 13
    その他chromatographed on an Isco 40 g silica cartridge
14. 14
    洗浄eluting with 4:1 hexane/EtOAc
15. 15
    その他to give a yellow oil that
16. 16
    workup.ADDITIONmix of desired material

実験手順

To a 250 mL round-bottom flask was added 2-bromo-1-methoxy-4-nitrobenzene (3.5 g, 15.08 mmol), copper(I) iodide (5.75 g, 30.2 mmol), and sodium 2,2,3,3,3-pentafluoropropanoate (5.25 g, 28.2 mmol) in DMF (75 ml) and toluene (25 ml) to give a tan suspension. The mixture was heated at 150° C. and toluene was removed by a Dean-Stark trap. The mixture was heated at 155° C. for 6 h under nitrogen, cooled and poured into 100 mL of water and 100 mL of ether, filtered through a 1-inch plug of Celite and the plug was rinsed with ether. The filtrate layers were separated. The organic layer was washed with brine, dried (Na2SO4) filtered and concentrated. The dark oil was flash chromatographed on an Isco 40 g silica cartridge eluting with 4:1 hexane/EtOAc to give a yellow oil that was a (3:1) mix of desired material and starting material (1.5 g, 37%).

出典