Reaction #2329

Reaction equation

Bromine

product

methyl 4-(2,2-dimethylacetyl)-phenoxyacetate

→

methyl 4-(2-bromo-2,2-dimethylacetyl)phenoxyacetate

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Otherthe solvent was evaporated in vacuo
2. 2
   Otherto give an orange oil
3. 3
   FiltrationA solution of this oil, in a small volume of dichloromethane, was filtered through silica
4. 4
   Otherthe clear filtrate, on evaporation

Procedure

Bromine (2.09 ml) was added dropwise over ten minutes to a stirred solution of the product of step (i) above (9.44 g) in carbon tetrachloride (200 ml). The solution was stirred for 16 hours, then the solvent was evaporated in vacuo to give an orange oil. A solution of this oil, in a small volume of dichloromethane, was filtered through silica and the clear filtrate, on evaporation, gave methyl 4-(2-bromo-2,2-dimethylacetyl)phenoxyacetate, 11.3 g, as a white crystalline solid: m.p. 46°-50° C.; NMR (d6DMSO) δ 8.09 (2H, d), 7.05 (2H, d), 4.92 (2H, s), 3.72 (3H, s), 2.0(6H, s).

Source