反应 #41762

反应方程式

dimethyl sulfate

5-fluoro-2-nitrophenylamine

trifluoroacetic anhydride

trifluoroacetamide

sodium hydroxide

→

(5-fluoro-2-nitrophenyl)methylamine

溶剂

methylenechloride

toluene

acetonitrile

反应条件

后处理

1. 1
   其他The mixture was quenched with saturated sodium bicarbonate solution
2. 2
   其他The organic layer was separated
3. 3
   洗涤washed with water, brine
4. 4
   其他dried
5. 5
   其他evaporated
6. 6
   workup.STIRRINGThe biphasic mixture was stirred overnight at room temperature
7. 7
   其他evaporated
8. 8
   洗涤washed with water, brine
9. 9
   其他dried
10. 10
    其他evaporated
11. 11
    其他The crude was purified by column chromatography
12. 12
    洗涤eluting with 1:1 hexanes and ethyl acetate

实验过程

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.

来源