반응 #53735

반응 방정식

water

hydrochloric acid

4-fluoro-1-methylsulfonyl-2-nitrobenzene

→

5-fluoro-2-methylsulfonylphenylamine

수율 96.5%

용매

ethanol

반응 조건

후처리

1. 1
   온도The reaction mixture is then heated at the
2. 2
   workup.ADDITIONare added portionwise
3. 3
   온도reflux of the solvent for 2 hours
4. 4
   여과It is then filtered through sintered glass
5. 5
   세척the solid is washed with ethanol
6. 6
   농축The filtrate is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
7. 7
   workup.ADDITIONThe residue is taken up in a mixture of water and ethyl acetate
8. 8
   추출The aqueous phase is extracted with 4 times 50 ml of ethyl acetate
9. 9
   세척washed with water
10. 10
    건조dried over magnesium sulfate
11. 11
    workup.ADDITIONtreated with 3S black
12. 12
    여과filtered
13. 13
    농축concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

실험 절차

5-Fluoro-2-methylsulfonylphenylamine can be obtained in the following way: 1.25 ml of water and 0.47 ml of an aqueous 12N hydrochloric acid solution are added to a solution of 1.2 g of 4-fluoro-1-methylsulfonyl-2-nitrobenzene in 80 ml of ethanol. The reaction mixture is then heated at the reflux of the solvent and 0.92 g of powdered iron are added portionwise. The reaction mixture is then stirred at the reflux of the solvent for 2 hours, then at a temperature in the region of 20° C. for 16 hours. It is then filtered through sintered glass and the solid is washed with ethanol. The filtrate is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is taken up in a mixture of water and ethyl acetate and then basified with an aqueous sodium hydrogencarbonate solution, to a pH in the region of 10, and allowed to settle out. The aqueous phase is extracted with 4 times 50 ml of ethyl acetate. The organic extracts are pooled, washed with water, dried over magnesium sulfate, treated with 3S black, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 1 g of 5-fluoro-2-methylsulfonylphenylamine is thus obtained in the form of a beige oil which crystallizes (Rf=0.33, silica gel thin layer chromatography, eluent: dichloromethane).

출처