Reaction #2319

Reaction equation

product

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

N-bromosuccinimide

→

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

Solvents

carbon tetrachloride

Conditions

Workup

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

Procedure

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).

Source