Reacción #2319

Ecuación de reacción

product

methyl N-[4-(acetyl)-phenoxyacetyl]glycinate

N-bromosuccinimide

→

methyl N-[4-(bromoacetyl)phenoxyacetyl]glycinate

Disolventes

carbon tetrachloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux temperature for 64 hours
2. 2
   OtroThe solvent was evaporated
3. 3
   workup.DISSOLUTIONthe black residue dissolved in methanol/ethyl acetate
4. 4
   workup.ADDITIONtreated with charcoal
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated
7. 7
   OtroThe resulting brown oil was purified by flash chromatography on silica
8. 8
   Lavadoeluting with dichloromethane

Procedimiento

The product of step (i) (3.00 g) and N-bromosuccinimide (2.02 g) in carbon tetrachloride (50 ml) was heated at reflux temperature for 64 hours. The solvent was evaporated and the black residue dissolved in methanol/ethyl acetate, treated with charcoal, filtered and then evaporated. The resulting brown oil was purified by flash chromatography on silica, eluting with dichloromethane. Trituration with hexane gave methyl N-[4-(bromoacetyl)phenoxyacetyl]glycinate, 0.85 g, as a solid: mp softens 109°-111° C.; NMR (d6DMSO) δ 8.60 (1H, bt), 7.99 (2H, d), 7.09 (2H, d), 4.84 (2H, s), 4.69 (2H, s), 3.91 (2H, d), 3.64 (3H, s).

Fuente