반응 #41762

반응 방정식

dimethyl sulfate

5-fluoro-2-nitrophenylamine

trifluoroacetic anhydride

trifluoroacetamide

sodium hydroxide

→

(5-fluoro-2-nitrophenyl)methylamine

용매

methylenechloride

toluene

acetonitrile

반응 조건

후처리

1. 1
   기타The mixture was quenched with saturated sodium bicarbonate solution
2. 2
   기타The organic layer was separated
3. 3
   세척washed with water, brine
4. 4
   기타dried
5. 5
   기타evaporated
6. 6
   workup.STIRRINGThe biphasic mixture was stirred overnight at room temperature
7. 7
   기타evaporated
8. 8
   세척washed with water, brine
9. 9
   기타dried
10. 10
    기타evaporated
11. 11
    기타The crude was purified by column chromatography
12. 12
    세척eluting with 1:1 hexanes and ethyl acetate

실험 절차

A solution of 5-fluoro-2-nitrophenylamine (1 eq) in methylenechloride was treated with trifluoroacetic anhydride (1 eq) and stirred for 10 minutes at 0° C. The mixture was quenched with saturated sodium bicarbonate solution. The organic layer was separated and washed with water, brine, dried and evaporated. To the solution of the trifluoroacetamide (1 eq) in a mixture of toluene, acetonitrile and sodium hydroxide solution (50%) was added benzyltrimethylammonium chloride (1 eq) and dimethyl sulfate (1.2 eq). The biphasic mixture was stirred overnight at room temperature and evaporated. The mixture was taken up in ethyl acetate, washed with water, brine, dried and evaporated. The crude was purified by column chromatography eluting with 1:1 hexanes and ethyl acetate to afford (5-fluoro-2-nitrophenyl)methylamine. MS: MH+=170.

출처