Reaction #41762

Reaction equation

dimethyl sulfate

5-fluoro-2-nitrophenylamine

trifluoroacetic anhydride

trifluoroacetamide

sodium hydroxide

→

(5-fluoro-2-nitrophenyl)methylamine

Solvents

methylenechloride

toluene

acetonitrile

Conditions

Workup

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

Procedure

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.

Source