Bromine → Methyl 4-(2,2-dimethylbromoacetyl)phenoxyacetate

HRID 2233Notes

Reaction equation

HRID 2233 reaction equation
[Br:1]Br.[CH3:3][CH:4]([CH3:19])[C:5]([C:7]1[CH:18]=[CH:17][C:10]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:8]=1)=[O:6]>C(Cl)(Cl)(Cl)Cl>[Br:1][C:4]([CH3:19])([CH3:3])[C:5]([C:7]1[CH:18]=[CH:17][C:10]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:8]=1)=[O:6]

Participants

4

Reactant 2

HCID 24408BromineHCID 12797090Methyl 2-(4-isobutyrylphenoxy)acetate

Product 1

HCID 18918473Methyl 4-(2,2-dimethylbromoacetyl)phenoxyacetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

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).

Workup

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

Sources & evidence

ORD record
ord-045379b86e3a4189977f9bacd7189198
Source dataset
uspto-grants-1998_03
Patent number
US05728701

Reaction notes

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