Reacción #2201630

Ecuación de reacción

trifluoroacetic acid

potassium fluoride

1,2-Dichloro-4-fluoro-5-nitrobenzene

ethyl glycolate

→

ethyl [(4,5-dichloro-2-nitrophenyl)oxy]acetate

Rendimiento 96.2%

Disolventes

CH3CN H2O

dioxane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrohad formed
2. 2
   Otroresulted in precipitation of the product
3. 3
   FiltraciónThe solid was filtered off
4. 4
   Otrodried under vacuum

Procedimiento

1,2-Dichloro-4-fluoro-5-nitrobenzene (50 g, 0.238 mol), ethyl glycolate (90.1 mL, 0.952 mol), and potassium fluoride (76.1 g, 1.31 mol) were added to a 1 L round-bottom flask containing 200 mL of anhydrous dioxane. The mixture was magnetically stirred and heated to 100° C. in an oil bath. After two hours, HPLC (Eclipse XDB-C18, 4.6×250 mm, 5 micron, 1-99% CH3CN/H2O with 0.1% trifluoroacetic acid) showed that all of the starting material (Rt=7.5 min) was gone and that one major peak (Rt=7.8 min) had formed. The reaction mixture was poured into 4 L of water, which resulted in precipitation of the product. The solid was filtered off and dried under vacuum to give ethyl [(4,5-dichloro-2-nitrophenyl)oxy]acetate (67.4 g, 0.229 mol, 96%) as a tan solid. MS (ES) m/e 294 [M+H]+.

Fuente