تفاعل #41762

معادلة التفاعل

dimethyl sulfate

5-fluoro-2-nitrophenylamine

trifluoroacetic anhydride

trifluoroacetamide

sodium hydroxide

→

(5-fluoro-2-nitrophenyl)methylamine

المذيبات

methylenechloride

toluene

acetonitrile

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر