反应详情

5.29 g iron filings, 240 mL of a 2/1 ethanol-water mixture, and 8.3 g 3,5-dichloro-4-(1-methyl-2,2,3,3,4,4,4-heptafluorobutoxy)nitrobenzene was stirred vigorously and heated under reflux while 2.0 mL conc. HCl in 2 mL ethanol was added dropwise. After one hour 2.0 mL conc. HCl in 2.0 mL ethanol was added and reflux was maintained for 6 hrs. Then added 2.0 mL conc. HCl in 3.0 mL ethanol and maintained reflux overnight. The mixture was filtered hot through Celite. The filtrate was concentrated under vacuum before being partitioned in saturated sodium bicarbonate and diethyl ether. The layers were separated and the aqueous layer was extracted with diethyl ether. The combined organics were washed with brine, dried (MgSO4), filtered, and concentrated to give 4.79 g of 3,5-Dichloro-4-(1-methyl-2,2,3,3,4,4,4-heptafluorobutoxy)aniline as an amber oil. 1H NMR and MS confirm pure product. Anal. calcd C11H8Cl2F7NO: C, 35.32; H, 2.16; N, 3.74. Found: C, 36.40; H, 2.33; N, 3.98.

1. temperatureheated
2. additionwas added dropwise
3. temperaturereflux
4. temperaturewas maintained for 6 hrs
5. temperaturemaintained
6. temperaturereflux overnight
7. filtrationThe mixture was filtered hot through Celite
8. concentrationThe filtrate was concentrated under vacuum
9. custombefore being partitioned in saturated sodium bicarbonate
10. customThe layers were separated
11. extractionthe aqueous layer was extracted with diethyl ether
12. washThe combined organics were washed with brine
13. dry with materialdried (MgSO4)
14. filtrationfiltered
15. concentrationconcentrated