Dimethyl Sulfate → (5-Fluoro-2-nitrophenyl)methanamine

Temperatur

0 °C

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.

1. customThe mixture was quenched with saturated sodium bicarbonate solution
2. customThe organic layer was separated
3. washwashed with water, brine
4. customdried
5. customevaporated
6. stirringThe biphasic mixture was stirred overnight at room temperature
7. customevaporated
8. washwashed with water, brine
9. customdried
10. customevaporated
11. customThe crude was purified by column chromatography
12. washeluting with 1:1 hexanes and ethyl acetate

ORD-Eintrag

ord-509ae7da801a4bffb137c61acb1593e7

Quelldatensatz

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08614330B2