2-Bromo-4-nitroanisole → Benzene, 1-methoxy-4-nitro-2-(1,1,2,2,2-pentafluoroethyl)-

Temperature

150 °C

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%).

1. customto give a tan suspension
2. customtoluene was removed by a Dean-Stark trap
3. temperatureThe mixture was heated at 155° C. for 6 h under nitrogen
4. temperaturecooled
5. additionpoured into 100 mL of water and 100 mL of ether
6. filtrationfiltered through a 1-inch plug of Celite
7. washthe plug was rinsed with ether
8. customThe filtrate layers were separated
9. washThe organic layer was washed with brine
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. concentrationconcentrated
13. customchromatographed on an Isco 40 g silica cartridge
14. washeluting with 4:1 hexane/EtOAc
15. customto give a yellow oil that
16. additionmix of desired material

ORD record

ord-8643760b00ff4365a20fb7274db56b44

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09095590B2